Tag: M.W=100-200

Application of 140-11-4, These common heterocyclic compound, 140-11-4, name is Benzyl acetate, 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.

In a 5 ml glass bottle into which the magnet was placed,Then add NaOEt (17 mg, 0.25 mmol),The catalyst E (0.38 mg, OOl mmol),Benzyl acetate (0. 7508 g, 5 mmol, S / C = 10000: 1),Solvent dioxane (2.5 mL),The above reaction system was placed in a high-pressure reactor, Replacement of hydrogen three times,Charged with hydrogen gas of 50 atm,The reaction vessel was placed in a 80 C oil bath,Heating and stirring 16h,The reaction vessel was cooled in an ice bath.The reaction system was analyzed by gas chromatography (SPBTM-5, FUSEDSILICA Capillary Column, 30mX0.25mmX0.25ym, filmthickness)Injection temperature of 250 C,Detection temperature 260 C, program temperature 120 C (0 C) -20 C / min to 240 C (Omin). Gas chromatographic analysis yielded 82%.

The synthetic route of 140-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WUHAN KAITE LISI TECHNOLOGY CO LTD; Zhang, Xumu; Tan, xuefeng; (15 pag.)CN104387418; (2016); B;,
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Some common heterocyclic compound, 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, molecular formula is C8H8ClNO2, 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. category: esters-buliding-blocks

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40872-87-5, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
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These common heterocyclic compound, 14064-10-9, name is Diethyl 2-chloromalonate, 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. Recommanded Product: 14064-10-9

General procedure: A mixture of diethyl chloromalonate (19.1 mmol) and suitable sodium phenate (20.1 mmol), prepared from an equivalent amount of the corresponding phenol and sodium in abs EtOH, was stirred and heated under reflux in acetone (100 mL) for 4 h. The solvent was removed under reduced pressure, the residue was taken up with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated to give an oily residue which was chromatographed on silica gel column (petroleum ether/ethyl acetate 9:1 as eluent). The desired compounds were obtained as pale yellow oils in 14-77percent yield.

The synthetic route of Diethyl 2-chloromalonate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fracchiolla, Giuseppe; Laghezza, Antonio; Piemontese, Luca; Parente, Mariagiovanna; Lavecchia, Antonio; Pochetti, Giorgio; Montanari, Roberta; Giovanni, Carmen Di; Carbonara, Giuseppe; Tortorella, Paolo; Novellino, Ettore; Loiodice, Fulvio; Bioorganic and Medicinal Chemistry; vol. 20; 6; (2012); p. 2141 – 2151;,
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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. 14064-10-9, name is Diethyl 2-chloromalonate, A new synthetic method of this compound is introduced below., SDS of cas: 14064-10-9

Step 1: 3,4-Dihydro-3-oxo-2H-pyrido[3,2-b]-1,4-oxazin-2-carboxylic Acid Ethyl Ester. Diethyl chloromalonate (9.73 g, 50 mmol) was added to a stirred mixture of 3-hydroxy-2-aminopyridine (5.51 g, 50 mmol), triethylamine (6.97 mL, 50 mmol) and EtOH (100 mL) at room temperature. The mixture was heated at reflux for 17 h and allowed to attain room temperature. The precipitate formed was filtered off, washed with EtOH and dried to give the product as a white solid: yield 3.85 g (35percent); mp 160-162° C. Anal. (C10H10N2O4) C, H, N.

The synthetic route of 14064-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Biovitrum AB; US6465467; (2002); B1;,
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Electric Literature of 25597-16-4, These common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, 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.

[0530] To a solution of 3-CHLORO-6-HYDROXY-2, 4-dimethylbenzaldehyde (6.9 g, 37.4 mmol) in 80 mL of DMF was added dried finely powdered K2CO3 (11.36 g, 82.2 mmol). With mechanical stirring, the reaction was heated to 65 C. To the suspension was added dropwise ethyl trifluorocrotonate (7.54 g, 44.9 mmol). The stirring reaction was heated at 90 C for 1.5 h. K2C03 was filtered from the cooled reaction. From the reaction under vacuum, DMF was removed. The resulting residue was dissolved in 400 mL EtOAc. The organic solution was washed with 100 mL 1 M KHS04, 70 mL OF SATD. KHC03, 100 mL brine, followed by drying over MGS04, and concentrating under vacuum. The crude desired product (13.8 g) of was isolated. After employing flash chromatography conditions, pure compound (9.8 g, 78 %) of was isolated and its structure confirmed by NMR and LC-MS.

Statistics shows that Ethyl 4,4,4-trifluorocrotonate is playing an increasingly important role. we look forward to future research findings about 25597-16-4.

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. 57486-67-6, name is Methyl 2-(2-fluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Methyl 2-(2-fluorophenyl)acetate

21.4 ml (21.4 mmol) of lithium hexamethyldisilazide (1.0 M in THF) were initially charged in THF (30 ml) under argon and a solution of 3.00 g (17.8 mmol) of methyl 2-fluorophenylacetate in THF (15 ml) was added dropwise at -78 C. The reaction mixture was stirred at -78 C. for 1 h, and then a solution of 3.80 g (21.4 mmol) of the compound from example 1A in THF (15 ml) was added dropwise. The solution was stirred at -78 C. for 1 h, then brought to RT, and saturated aqueous ammonium chloride solution was added in portions. The mixture was diluted with water and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated. The residue was stirred with MTBE, the solid was filtered off and the filtrate was concentrated. Silica gel chromatography (mobile phase: cyclohexane-ethyl acetate: 30:1, 20:1) of the residue gave 3.66 g (87% pure, 57% of theory) of the title compound. The crude product was reacted without further purification. [0195] LC-MS (method 1): Rt=1.05 min; MS (ESIpos): m/z=310 (M+H)+. [0196] 1H NMR (400 MHz, DMSO-d6): delta=3.66 (s, 3H), 6.25 (s, 1H), 7.20-7.28 (m, 4H), 7.31-7.38 (m, 1H), 8.15-8.23 (m, 1H), 8.68-8.71 (m, 1H).

According to the analysis of related databases, 57486-67-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Follmann, Markus; Stasch, Johannes-Peter; Redlich, Gorden; Ackerstaff, Jens; Griebenow, Nils; Knorr, Andreas; Wunder, Frank; Li, Volkhart Min-Jian; Mittendorf, Joachim; Schlemmer, Karl-Heinz; Jautelat, Rolf; US2013/267548; (2013); A1;,
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Application of 4911-54-0,Some common heterocyclic compound, 4911-54-0, name is Ethyl 4-methylpent-4-enoate, molecular formula is C8H14O2, 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.

To a flame-dried flask that was purged under argon for 20 min was added LiAlH4 followed by 150 mL of anhydrous THF. The reaction mixture was cooled to 00C and a solution of compound 7 in THF (20 mL) was added slowly. The resulting solution was allowed to warm to room temperature and was stirred for 3 h until the starting material was completely consumed as indicated by TLC. The reaction was quenched by slow addition of the mixture to 300 mL of ice cold IM NaOH. The mixture was then allowed to stir for another hour and was filtered through Celite. A large amount of diethyl ether was used for rinsing. The filtrate was treated with water and extracted twice with diethyl ether. The combined organic phase was dried over Na2SO4 and evaporated in vacuo to give a residue which was purified via distillation at 20 mm Hg (bp 65-68 0C) to afford compound 8 as a yellow oil (9.5 g, 0.095 mol, 79%) (Mazzocchi et al. (1983) J. Org. Chem. 48, 2981-2989).1H NMR (500 MHz, CDCl3) delta 1.47 (br, IH), 1.69-1.74 (m, 5H), 2.1 (t, J = 7.5 Hz, 2H), 3.66 (t, J = 6.5 Hz, 2H), 4.71 (d, J = 0.8 Hz, IH), 4.73 (d, J = 0.8 Hz, IH), 4.73 (d, J = 0.4 Hz, IH); 13C NMR (125 MHz, CDCl3), delta 22.22, 30.41, 33.98, 62.64, 1 10.08, 145.40.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-methylpent-4-enoate, its application will become more common.

Reference:
Patent; PARHAMI, Farhad; KIM, Woo-Kyun; WO2008/82520; (2008); A2;,
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These common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, 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. Application In Synthesis of Methyl 3-bromopropiolate

To a stirring solution of1,8-dihydroxynaphthalene (2) (1.74 g, 10.9 mmol) and methyl 3-bromopropiolate32 (2.65 g, 16.3 mmol)in anhydrous CH2Cl2 (40 mL) was added DABCO (2.66 g, 21.8 mmol) at 0 C under an argon atmosphere.After being stirred at room temperature for 3 h, the reaction mixture was treated with 1 M aqueous HCl.The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with brine,dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatographyeluting with 25% EtOAc/hexane to yield the title compound (2.17 g, 8.96 mmol, 82%) as a white solid. Rf0.34 (20% EtOAc/hexane). Mp 115-118 C. IR nu (neat, cm-1): 1721, 1654, 1602, 1419, 1381, 1281, 1248,1131, 1089, 815, 799, 753. 1H-NMR (400 MHz, CDCl3): delta 7.52 (d, J = 8.3 Hz, 1H), 7.51 (d, J = 8.3 Hz,1H), 7.45 (dd, J = 8.3, 7.6 Hz, 1H), 7.42 (dd, J = 8.3, 7.3 Hz, 1H), 7.13 (d, J = 7.3 Hz, 1H), 6.93 (d, J =7.6 Hz, 1H), 4.97 (s, 1H), 3.75 (s, 3H). 13C-NMR (100 MHz, CDCl3): delta 166.2, 158.6, 144.4, 144.1, 133.6,128.0, 127.8, 121.9, 121.7, 110.6, 108.4, 107.6, 78.2, 50.9. HRMS (ESI, [M+H]+): calcd for C14H11O4,243.0652; found, 243.0653

The synthetic route of Methyl 3-bromopropiolate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tsukamoto, Hirokazu; Nomura, Yumi; Doi, Takayuki; Heterocycles; vol. 99; 1; (2019); p. 549 – 565;,
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Synthetic Route of 18595-14-7,Some common heterocyclic compound, 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, molecular formula is C9H11NO2, 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.

1.0016 g (8.1358 mmol) of pyridine-4-carboxylic acid dissolvedin 10 mL of thionyl chloride was stirred and refluxed for 3 h. Then1.3423 g (8.1258 mmol) of methyl-4-amino-3-methylbenzoate wasadded in 35 mL of chloroform into the precipitated acid chloride. The reaction mixture was heated with stirring for another 2 h and ayellow powder precipitated.2.2500 g (7.3351 mmol, yield ca.: 90%, Anal. Cal. C15H15Cl1N2O3[%]: C, 58.73; H, 4.93; N, 9.13; Found: C, 58.57; H, 4.66; N, 9.13) ofobtained powder was filtered and washed with chloroform anddiethyl ether. The yellow needles precipitated after recrystallizationfrom acetonitrile/MeOH solution mixture. 1H NMR (600 MHz,MeOD) delta 10.61 (s, 1H), 9.14-9.06 (m, 1H), 8.56 (d, J 6.5 Hz, 1H),7.99 (dd, J 1.4, 0.4 Hz, 1H), 7.92 (dd, J 8.3, 1.7 Hz, 1H), 7.65 (d,J 8.3 Hz, 1H), 3.92 (s, 1H), 2.41 (s, 1H). 13C NMR (151 MHz, MeOD)delta 168.16, 163.71, 152.05, 144.43, 140.80, 135.13, 133.23, 129.95,128.93, 127.12, 126.99, 52.83, 18.36. FT-IR (KBr, cm1): 3436 n(O-HKBr), 3241 n(N-H), 3170, 3105, 3053, 3010, 2955, 2866 n(C-H),1712, 1689 n(C]O), 1633-1434 n(ringC]C), 1315e1139 n(C-O) and(C-N) overlapped, 840, 770, 647 d(C-H ringC]C)oop.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kwiatek, Dorota; Kubicki, Maciej; Skokowski, Przemys?aw; Gruszczy?ska, Joanna; Lis, Stefan; Hnatejko, Zbigniew; Journal of Molecular Structure; vol. 1178; (2019); p. 669 – 681;,
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Synthetic Route of 3196-15-4,Some common heterocyclic compound, 3196-15-4, name is Methyl 2-bromobutyrate, molecular formula is C5H9BrO2, 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.

To a solution of pyridine-3-carbothioamide (1 g, 7.24 mmol) in EtOH (15 mL) and pyridine (1 mL, 12.3 mmol) was added methyl 2-bromobutanoate (1 mL, 8.68 mmol). The mixture was heated at reflux for 18 hours, after which it was cooled and concentrated. The crude 5-Ethyl-2-pyridin-3-yl-thiazol-4-ol was then redissolved in DMF (36 mL) at 0 C., and to the mixture was added 60% sodium hydride (751 mg, 18.8 mmol). After stirring for 15 min at rt, 1,1,1-trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide (3.87 g, 10.8 mmol) was added. The mixture was reacted for 20 min, quenched with sat. NH4Cl, diluted with diethyl ether. The mixture was washed with water, and then brine. The organic layer was concentrated, and the resulting material chromatographed (5-55% EtOAc/Hexanes to give trifluoro-methanesulfonic acid 5-ethyl-2-pyridin-3-yl-thiazol-4-yl ester (0.85 g) as an orange oil.

The synthetic route of 3196-15-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Alam, Muzaffar; Du Bois, Daisy Jo; Hawley, Ronald Charles; Minatti, Ana Elena; Kennedy-Smith, Joshua; Thakkar, Kshitij Chhabilbhai; Wilhelm, Robert Stephen; US2013/158066; (2013); A1;,
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