Tag: M.W=100-200

Synthetic Route of 178312-47-5,Some common heterocyclic compound, 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, molecular formula is C9H14F2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution ofbutyllithium(2.000 mL, 2.80 mmol) was added to a cold (-78 C.) solution ofdiisopropylamine(0.396 mL, 2.80 mmol) inTHF(5 mL) under N2and the mixture was stirred at -78 C. for 1 h. A solution ofethyl 4,4-difluorocyclohexanecarboxylate(384 mg, 2 mmol) in THF (2 mL) was added at -78 C. and the mixture was stirred for 1 h and then gradually warmed to -20 C. over 2 h and then re-cooled to -78 C. Neat((chloromethoxy)methyl)benzene(0.226 mL, 2.200 mmol) was added and the mixture was allowed to warm to rt over 2 h. The reaction was quenched with satd. NH4Cl and extracted with EtOAc and washed with water, brine, dried (Na2SO4). Evaporation of the solvent afforded a lightyellowoil which was purified by silica gel FCC (1:1 DCM-hexanes) to afford1-((benzyloxy)methyl)-4,4-difluorocyclohexanecarboxylateas acolorlessoil.

The synthetic route of 178312-47-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hewawasam, Piyasena; Lopez, Omar D.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Kadow, John F.; Meanwell, Nicholas A.; Gupta, Samayamuthula Venkata Satya Arun Kumar; Kumar, Indasi J. Gopi; Ponugupati, Suresh Kumar; Belema, Makonen; US2015/23913; (2015); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 23680-40-2 as follows. SDS of cas: 23680-40-2

Methyl 3-bromopropiolate (1 13 g, 698 mmol) and freshly cracked cyclopentadiene (92 g, 1 .39 mol) were dissolved in toluene (570 ml_) and heated to 90 C, under nitrogen for 2 hr. The reaction was cooled to room temperature, and the toluene evaporated in vacuo to give a dark brown oil. This was azeotroped three times with acetonitrile to remove excess dicyclopentadiene, giving the title compound (1 19 g, 74% yield) as a brown oil. 1 H NMR (400 MHz, CDCI3) delta ppm 6.88 – 6.94 (m, 1 H), 6.85 (ddd, J = 5.2, 3.1 , 1 .0 Hz, 1 H), 4.00 (dqd, J = 2.8, 1 .7, 0.8 Hz, 1 H), 3.76 (s, 3 H), 3.69 (ddtd, J = 3.2, 2.4, 1 .5, 0.7 Hz, 1 H), 2.32 (dt, J = 6.7, 1 .7 Hz, 1 H), 2.13 (dt, J = 6.7, 1 .7 Hz, 1 H).

According to the analysis of related databases, 23680-40-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BURNS, Aaron Craig; COLLINS, Michael Raymond; GREASLEY, Samantha Elizabeth; HOFFMAN, Robert Louis; HUANG, Qinhua; KANIA, Robert Steven; KUNG, Pei-Pei; LINTON, Maria Angelica; NARASIMHAN, Lakshmi Sourirajan; RICHARDSON, Paul Francis; RICHTER, Daniel Tyler; SMITH, Graham; WO2015/166373; (2015); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 394-35-4, name is Methyl 2-fluorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 394-35-4

General procedure: Different substituted carboxylic acids (20 mmol) (A) were stirred with thionyl chloride (100 mmol) in dry methanol (75 ml) or 5?6 h to synthesize corresponding methyl esters (B) (Scheme1). After extraction of esters in chloroform, solvent was evaporated and esters (66 mmol) were refluxed with hydrazine hydrate(330 mmol) in ethanol (75 ml) for 4?5 h. A solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with hexane to afford hydrazide ligand (C). The spectral and analytical data are given below.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Ain, Qurrat Ul; Ashiq, Uzma; Jamal, Rifat Ara; Mahrooof-Tahir, Mohammad; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 115; (2013); p. 683 – 689;,
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Related Products of 2905-65-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2905-65-9 as follows.

This example illustrates the tandem Ir-catalyzed borylation and catalytic amination process. [0064] 3-Aminoboronic acids and esters as shown below are of interest as evidenced by the large number of derivatives synthesized, and by several patents, which note their activity as O-lactamase inhibitors (See, for example, Shoichet et al., WO0035905). Few in number, however, are 1, 3, 5-aminoboronic acids and esters (about 25 compounds by SCIFINDER SCHOLAR). Such substrates may prove useful for further derivatization as they can possess three unique sites for diversity. Furthermore, these compounds may prove ideal as scaffolds for combinatorial libraries. The boronic acid or ester can be transformed into a myriad of functionalities including aryl or vinyl via the Suzuki-Miyuara coupling (Miyaura and Suzuki, Chem. Rev. 95: 2457-2483 (1995); Suzuki, J. Organomet. Chem. 576: 147-168 (1999); Miyaura, In Advances in Metal-Organic Chemistry: Liebeskind, Ed.: JAI: London,; Vol. 6, pp. 187-243 (1998)). If R is a halogen, then there exists a multitude of coupling opportunities (See, for examples, Metal-catalyzed Cross-coupling Reactions; Diederich and Stang, eds.: Wiley: Wienheim, 1998). [0066] Recently, a catalytic aromatic C-H activation/borylation reaction utilizing Ir- or Rh-catalysts was developed. The process is high yielding, functional group tolerant (alkyl, halo, carboxy, alkoxy, and protected amino), chemoselective (1,3-substited arenes give only the 5-boryl product), and efficient (Iverson and Smith, J. Am. Chem. Soc. 121: 7696-7697 (1999); Cho et al., J. Am. Chem. Soc. 122: 12868-12869 (2000); Tse et al., Org. Lett. 3: 2831 (2001); Chao et al., Science 295: 305-308 (2002)). Furthermore, the process allows for the direct construction of aryl boronic esters from hydrocarbon feedstocks without going through an aryl halide. Scheme 2 depicts a prototypical borylation reaction: borylation of benzene using (Ind)Ir(COD)(2 mol %), dppe (2 mol %). The borane of choice is pinacolborane (HBPin). A variety of Ir(I) catalysts can be used, including [Ir(COD)Cl]2, Ir(Indenyl)(C2H4)2, Ir(Indenyl)dppe, and (Indenyl)Ir(COD), in the presence of 2 mol equivalents of PMe3 or 1 mol equivalent of a bidentate ligand like dmpe or dppe. The catalyst system of choice is (Indenyl)Ir(COD), dppe or dmpe (2 mol % each) because of it’s cleanness of reaction and efficient TOF (24 h-1 with benzene). The reaction can be run in the neat arene or in inert solvents (e.g. cyclohexane). During our studies into tandem borylation/Suzuki coupling, we noted difficulties with the hydrolysis of the boronic ester functionality (Bpin). The robustness of the BPin group suggested that, perhaps, the pinacol might serve as a protecting group for the boron. Thus, it was deemed of interest to explore other catalytic transformations in the presence of the BPin group. One such transformation is the Buchwald-Hartwig amination of aryl halides (See, for example; Wolfe et al.,. J. Org. Chem. 65: 1158 (2000); Hartwig et al., J. Org. Chem. 64: 5575 (1999); Wolfe and Buchwald, Angew. Chem. Int. Ed. 38: 2413 (1999)). Initially, the reaction was attempted on pure 1-chloro-3-methylphenyl-5-BPin. As shown in Scheme 3 (Buchwald-Hartwig coupling of 1-chloro-3-methylphenyl-5-BPin with aniline), application of Buchwalds protocol proceeded cleanly to give the desired cross-coupling product in 64.7% and 63.8% yield. The use of PtBu3 improved the yield to 78.8%. Unfortunately, initial attempts to perform the reaction in the ?one-pot? protocol were unsuccessful. Table 1 summarizes the results. In all cases where K3PO4.nH2O was used, a significant amount of pinacol was observed by GC-FID (Entries 1-5). While this is indicative of reaction of the BPin group and is most likely a by-product of Suzuki coupling (in this case, dimerization or oligiomerization of the starting material), no dimers or oligiomers were isolated. Noteworthy, is the formation of the desired product, albeit in low yield (10% GC-FID ratio), using K3PO4.nH2O and PtBu3 when all other attempts using the base failed. With anhydrous K3PO4, results were better (Entries 6-9). Most importantly, no pinacol was formed in these reactions. Changing the base or increasing catalyst loading did not improve the results. The use of PtBu3 led to the best results and after 4 days at 100 C., 34.4% of the desired product was isolated (Entry 10). This result, however, falls short of the reaction performed on pure material and shows that the by-products from the Ir-catalyzed borylation are not completely innocuous. As was previously mentioned, a potential source of concern is the presence of free bidentate phosphines after the borylation, which may interfere with subsequent reactions. In the tandem Suzuki reactions, an aryl chloride was successfully coupled only when dmpe was used as the Ir ligand. Thus, the tandem borylation/Buchwald-Hartwig amination reaction of the present invention was attempted using the (Ind)Ir(COD)/dmpe precatalyst….

According to the analysis of related databases, 2905-65-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Board of Trustees of Michigan State University; US2004/24237; (2004); A1;,
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Reference of 369-26-6,Some common heterocyclic compound, 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, molecular formula is C8H8FNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Methyl 3-amino-4-fluorobenzoate (275mg) and DMAP (100mg) were dissolved in pyridine (lOml). Then cyclopropanesulfonyl chloride (330mg) was added into the solution. The reaction mixture was heated to 110¡ãC and stirred for 12 hours until the reaction is complete. The solvent was stripped off, the solid was dissolved in CH2C12 (50m1) followed by iN HC1 solution (50m1). The bottom aqueous layer was split off and the organic layer was washed with water and dried by anhydrous Na2SO4. The CH2C12 was stripped off and 270mg of methyl 3 -(cyclopropanesulfonamido)-4-fluorobenzoate was used for the next step directly.

The synthetic route of 369-26-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHILADELPHIA HEALTH & EDUCATION CORPORATION, D/B/A DREXEL; INSTITUTE FOR HEPATITIS AND VIRUS RESEARCH; ENANTIGEN THERAPEUTICS, INC.; BAUGH, Simon David Peter; YE, Hong; XU, Xiaodong; GUO, Ju-tao; XIAO, Tong; DU, Yanming; BLOCK, Timothy; WO2014/106019; (2014); A2;,
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Adding a certain compound to certain chemical reactions, such as: 7335-27-5, name is Ethyl 4-chlorobenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7335-27-5, HPLC of Formula: C9H9ClO2

General procedure: A 5 mL absolute ethanol solution of hydrazine hydrate (80%) and Compound I (6 mmol) was refluxed for 4-6 h under severely stirring, the product being appeared as yellowish white solid. For purification of product, it was filtered and washed with 30 mL water and 30 mL ethanol pre-cooled by ice, and recrystallized from ethanol to yield the Compound II as white solid. 4-chlorobenzohydrazide (II-1): yield (91.3%). Melting point: 143.6-144.1 C. ESI-MS (m/z, [M+H]+) = 171.2.

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Reference:
Article; Liu, Lizeng; Meng, Xianfang; Li, Wei; Zhou, Xueqin; Bai, Zhengchen; Liu, Dongzhi; Lv, Yunrong; Li, Rui-Hong; Dyes and Pigments; vol. 108; (2014); p. 32 – 40;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 24812-90-6

Anhydrous p-toluene sulfonic acid (41.99 g, 220.8 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (20 g, 110.38 mmol) obtained in step 1 and benzonitrile (22.77 g, 220.8 mmol) were added thereto and stirred at 180 C for 5 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgS04 and concentrated under a reduced pressure. The concentrate was dissolved in 50 % methanol and 5 % NaOCl (56 ml, 37.65 mmol) was added dropwise thereto. After 5 min, the resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chlomatography (eluent-MeOH/CDCl3=5:95, Merck, Silicagel 60) to obtain the title compound (31 g, 25.10 mmol) in a yield of 88 %. 1H NMR (CDCl3): delta 7.78 (1H, d), 7.48 (1H, s), 7.37-7.24 (5H, m), 6.95 (1H, d), 3.78 (6H, s) MW: 318

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 24812-90-6.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 6933-47-7, name is Methyl 4-amino-2-methylbenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

General procedure: To a stirred solution of tert-butyl 2-formyl-6-azaspiro[3.4]octane-6-carboxylate (CAS: 203662-55-9) (225 mg, 1.0 mmol) and 2-(3-aminopheny])acetonitrile (CAS: 4623-249) (136 mg, 1.03 mmol) in MeOH (10 mL) at room temperature was added decaborane (43 mg, 0.35 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated. The residue was purified bysilica gel chromatography eluted with PE/EtOAc(3/1,v/v) to afford intermediate 119 (340 mg, 99% yield) as a yellow solid. Intermediate 178 was prepared via an analogous reaction protocol as described forthe preparation of intermediate 119, starting from the respective starting materials.

The synthetic route of 6933-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; JOHNSON & JOHNSON (CHINA) INVESTMENT LTD.; DAI, Xuedong; QUEROLLE, Olivier Alexis Georges; KROSKY, Daniel Jason; CAI, Wei; FU, Liqiang; KONG, Linglong; LIU, Yingtao; WAN, Zhao-Kui; HERKERT, Barbara; PANDE, Vineet; EDWARDS, James Patrick; PATRICK, Aaron Nathaniel; ANGIBAUD, Patrick Rene; PONCELET, Virginie Sophie; (488 pag.)WO2019/120209; (2019); A1;,
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Reference of 25597-16-4, A common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[0832] A mixture of 10 g (72.5 mmol) of 2, 4-dihydroxybenzaldehyde, 15.3 mL (101. 4 mmol) of ethyl 4-triflouromethylcrotonate, and 20 g (145 mmol) of potassium carbonate in 25 ML of anhydrous DIMETHYLFORMMAMIDE was heated to 90C for three h. After cooling to room temperature, the reaction was added to 500 mL of ethyl acetate. The organic phase was washed with brine three times, dried over anhydrous magnesium sulfate and CONCD in vacuo. Silica chromatography with EtOAc/hexane (3: 7) gave 19.0 g (98%) of a yellow solid: 1H NMR (CDC13/400 MHz) 7.63 (s, 1H), 6.85 (d, J=8. 8 Hz, 1H), 6.79 (dd, J=8.8Hz, 2.8Hz, 1H), 6.70 (d, J=2. 8 Hz, 1H), 5.63 (q, J=6. 8 Hz, 1H), 4. 31 (m, 2H), 1.34 (t, J=7. 2 Hz, 3H). MS (ESI+) 289. 1 (M+1, 100).

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 50413-30-4, name is Methyl 2-amino-4-methoxylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-amino-4-methoxylbenzoate

Example 1 : methyl 4-methoxy-2-[(3-UQ-methgammal-lH-imidazol-4-yl)sulfonyllamino} quinoxalin-2-yl)aminolbenzoate; N-(3-chloroquinoxalin-2-yl)-l -methyl- lH-imidazole-4-sulfonamide (2 g; 6.2 mmol; 1 eq) and methyl 2-amino-4-methoxybenzoate (1.2 g; 6.8 mmol; 1.1 eq) are taken up in water (60 mL) and acetic acid (160 muL; 3.65 mmol; 0.6 eq) is added. The suspension is heated up to 1700C in the microwave under normal absorption for 20 min. The reaction is stopped by filtration of the solid and washing with water until neutral. The orange powder obtained is dried under vaccum at 400C overnight then taken up in DCM. Triethylamine (1.72 mL) is added. After sonication, the solvents are removed under reduced pressure and the residue obtained is washed with water then dried under vacuum at 400C overnight. The powder is taken up in MeOH and refluxed then the suspension is left at 4C for Ih. The precipitate is filtered and washed with MeOH then dried under vacuum at 4O0C for 2 days, to afford 1.68 g (58%) of the title compound as a yellow powder. 1H NMR (DMSO-Ci6) O 11.77 (s, IH), 9.05 (d, J= 2.3 Hz, IH), 8.10-7.95 (m, 2H), 7.90 (s, IH), 7.85-7.76 (m, IH), 7.73-7.60 (m, IH), 7.55-7.35 (m, 2H), 6.73 (dd, J= 8.6, 2.2 Hz, IH), 3.91 (s, 6H), 3.72 (s, 3H). HPLC (max plot) 100%; Rt 4.12 min. LC/MS: (ES+): 469.0, (ES-): 467.1 .

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 50413-30-4.

Reference:
Patent; LABORATOIRES SERONO SA; WO2008/101979; (2008); A1;,
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