Tag: M.W=200-300

Reference of 14273-90-6, 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. 14273-90-6, name is Methyl 6-bromohexanoate, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of hexane washed sodium hydride (216 mg, 4.32 mmol) in 5 mL of DMF was added a solution of (R,R)-3-hydroxyphenyl-2-propyl-N-formamido-N-alpha-methylbenzylamine (compound 5 of FIG. 6) (1.22 g, 4.32 mmol). After stirring for 30 min at room temperature, a solution of methyl 6-bromohexanoate (1.36 g, 6.48 mmol) in DMF (3 mL) was added and stirred overnight at room temperature. The reaction mixture was diluted with H2O (50 mL) and extracted with methylene chloride (3×10 mL). The combined organic fraction was washed with saturated sodium chloride solution and dried over Na2SO4. After removal of the solvent, the residue was purified on a silica gel column. Eluting with a solvent mixture (CH2Cl2:hexane:MeOH, 4:14:1) to give 1.68 g (95percent) of compound 6 of FIG. 6. 1H NMR (CDCl3) delta1.28 (dd, 3H), 1.53 (m, 2H), 1.58 (dd, 3H), 1.72 (m, 4H), 2.36 (m, 2H), 2.41 (m, 1H), 2.89 (m, 1H), 3.25 (m, 1H), 3.41 (t, 2H), 3.68 (s, 3H), 3.82 (q, 2H), 4.58, 6.07 (2 q, 1H), 6.17, 6.67 (2 s, 1H), 6.57, 6.40 (2d, 1H), 6.67 (dd, 1H), 7.05 (dd, 1H), 7.36 (m, 5H), 8.41, and 8.48 (two s, 1H). The sample was used in the next step without further characterization. (0217) A solution of the above formamide compound 6 of FIG. 6 (1.63 g) was treated with BH3.THF (10 mL) and stirred for 30 min when the excess of BH3 was decomposed with MeOH followed by dilute HCl. The reaction mixture was basified with dilute NH4OH and extracted with methylene chloride (3×25 mL). The organic fraction was dried over Na2SO4 and evaporated to dryness. The oily material was dissolved in MeOH (25 mL), and Pd/C (250 mg) was added. The mixture was heated to reflux with formic acid (3 mL in three portions) for an hour. The filtrate, obtained after removal of the catalyst, was evaporated and the resulting residue purified on a silica gel column. Elution with 10percent MeOH in methylene chloride gave 0.84 g (70percent overall in two steps) of a clear oil compound 8. 1H NMR (CDCl3) 1.06 (d, 3H), 1.50 (m, 2H), 1.71 (m, 2H), 1.80 (m, 2H), 2.33 (t, 2H), 2.41 (s, 3H), 3.67 (s, 3H), 3.95 (t, 2H), 6.75 (m, 3H), 7.19 (m, 1H). The sample was converted to HCl salt; mp 53-57° C. Elemental analysis: calcd. for C17H27NO3.HCl.0.75 H2O: C, 59.50; H, 8.50; N, 4.10. Found: C, 59.65; H, 8.45; N, 4.21

The chemical industry reduces the impact on the environment during synthesis Methyl 6-bromohexanoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Board of Trustees of the University of Arkansas; Owens, Samuel M.; Carroll, Frank Ivy; Abraham, Philip; (77 pag.)US9303092; (2016); B2;,
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Some common heterocyclic compound, 150529-73-0, name is Methyl 2-(3-bromophenyl)acetate, molecular formula is C9H9BrO2, 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. Safety of Methyl 2-(3-bromophenyl)acetate

A solution of the bromide from preparation 26 (15.0g, 65.0mmol), tributyltin methoxide (28.3ml, 98mmol), isopropenyl acetate (10.8ml, 98.0mmol), palladium(ll) acetate (750mg, 3.30mmol) and tri-orffto-tolylphosphine (2.0g, 6.5 mmol) were stirred together in toluene (75ml) at 100C under nitrogen for 5 hours. After cooling the reaction was diluted with ethyl acetate (1 50ml) and 4M aqueous potassium fluoride solution (90ml) and stirred for 15 minutes. The mixture was filtered through arbocel and the organic phase separated and reduced in vacua. The residue was purified by flash column chromatography silica gel eluting with a solvent gradient of diethyl ether:pentane:dichloromethane (0:100:0 changing to 25:75:0 then to 0:0:100, by volume) to give the title compound as a pale yellow oil (12.6g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 150529-73-0, its application will become more common.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/108675; (2004); A1;,
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Related Products of 3650-78-0,Some common heterocyclic compound, 3650-78-0, name is Methyl 3-(4-bromophenyl)acrylate, molecular formula is C10H9BrO2, 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.

Compound (7.5 g) obtained from step a above, pyridine-2-methoxy-5-boronic acid (9.48 g), tetrakistriphenylphosphinepalladium (0) (1.79 g) and potassium carbonate (12.83 g) were taken in dimethylformamide (60 mL) under nitrogen atmosphere. The reaction mixture was refluxed under nitrogen atmosphere for 6 hours. After cooling to room temperature, water was added and the reaction mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over anhydrous sodium sulfate and the solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash column chromatography using 20-30 % ethyl acetate in hexane to get the title compound (8.09 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-(4-bromophenyl)acrylate, its application will become more common.

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2008/23336; (2008); A2;,
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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. 206551-41-9, name is Methyl 3-bromo-2-fluorobenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C8H6BrFO2

In a 500 mL flask was placed 1 ,1-diotamethylethyl carbamate (6 03 g, 51 5 mmol), methyl 3-bromo-2-fluorobenzoate (10 g, 42 9 mmol), Pd2(dba)3 CHCI3 (0 89 g, 0 86 mmol), xantphos (1 49 g, 2 57 mmol) and cesium carbonate (16 8 g, 51 5 mmol) The flask was sealed with a rubber septum, placed under high vac, and toluene (200 mL) was added Three cycles of high vac/N2 were performed and the reaction 25 mixture was stirred at 90 C overnight The reaction was filtered through a pad of celite with EtOAc washing and concentrated To the residue was added DCM (200 mL) followed by TFA (50 mL, 649 mmol), and the mixture was stirred at rt for 1 h The volatiles were removed under reduced pressure and the residue was taken up in EtOAc and washed with saturated NaHCO3 and brine The organic layer was dried over sodium sulfate and stripped onto silica and column chromatographed on silica with 5% to 50% EtOAc Hexane to give 5 53 g (76%) of the title compound of Step B 1H-NMR (400 MHz, DMSO-d6) delta 6 92 – 7 01 (m, 3 H), 5 37 (s, 2 H), and 3 81 (s, 3 H) MS (ESI) 170 [M+H]+

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:
Patent; GLAXOSMITHKLINE LLC; ADJABENG, George; BAUM, Erich; BIFULCO, Neil; DAVIS-WARD, Ronda, G.; DICKERSON, Scott, Howard; DONALDSON, Kelly, Horne; HORNBERGER, Keith; PETROV, Kimberly; RHEAULT, Tara, Renae; SAMMOND, Douglas, McCord; SCHAAF, Gregory, M.; STELLWAGEN, John; UEHLING, David, Edward; WATERSON, Alex, Gregory; WO2010/104899; (2010); A1;,
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Application of 59227-79-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 59227-79-1, name is Ethyl 4-(4-chlorophenoxy)butanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Hydrazine hydrate (0.060 mol) was added to the solution of compounds 3a-h (0.045 mol) in ethanol (25 ml), and the reaction mixture was stirred at room temperature for 4 h. Reaction completion was monitored by thin-layer chromatography using hexane: ethyl acetate (2:1) as the mobile phase and allowed to stand overnight. Formed white crystals 4a-h were filtered, washed, and after drying recrystallized from ethanol to give 4a-h.

The synthetic route of Ethyl 4-(4-chlorophenoxy)butanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Al-Ghorbani, Mohammed M. Abdullah; Indian Journal of Heterocyclic Chemistry; vol. 28; 3; (2018); p. 379 – 384;,
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Electric Literature of 721-63-1, 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 721-63-1 as follows.

General procedure: Arylacetate(0.05mol) was dissolved in dry THF or toluene, and stirred in the ice bath.Sodium (0.075mol) was added to the solution, the mixture was stirred for 30 minin the ice bath. Ethyl formate (0.1mol) was added by dropwise to the above solution,the temperature of the reaction mixture was maintained at < 5 C.After the addition, the reaction mixture was stirred for another 2 h, thenwarmed to room temperature and stirred overnight (about 15 h). Water (50mL) wasadded to the slurry mixture, and stirred for an additional 30 min, thenportioned between organic layer and water. Water layer was extracted withdichloromethane (2×50mL). These extracts were discarded. The aqueous phase wasacidified with acetic acid or 5% hydrochloric acid, and extracted withdichloromethane (3×50mL). This extract was washed with water and brine, driedover anhydrous sodium sulfate, and the solvent was removed by rotaryevaporation under reduced pressure to give thick yellow oil, which was purifiedby column chromatography with ethyl acetate in petroleum ether. According to the analysis of related databases, 721-63-1, the application of this compound in the production field has become more and more popular. Reference:
Article; Liu, Jinbing; Chen, Changhong; Wu, Fengyan; Tang, Junyuan; Bioorganic and Medicinal Chemistry Letters; vol. 26; 7; (2016); p. 1715 – 1719;,
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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. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, A new synthetic method of this compound is introduced below., Application In Synthesis of Diethyl 2-bromo-2-methylmalonate

General procedure: To a 7 mL vial equipped with magnetic stir bar was added bromomalonate (1.0 equiv,0.40 mmol), 2,6-lutidine (1.0 equiv, 0.40 mmol), tris[2-phenylpyridinato-C2,N]iridium(III) (1 mol %, 4.0 mumol), and heterocycle (5.0 equiv, 2.0 mmol). Dryacetonitrile or DMA (0.5 mL, 0.8 M) was then added and the reaction was sparged withN2 for 15 min. The reaction was set to stir under nitrogen at room temperature surroundedby a string of 1W or two strings of 4W blue LEDs for 24 h. The reaction mixture wasthen diluted with ethyl acetate and extracted with water. The aqueous layer was extractedwith ethyl acetate (2 x 10 mL). The combined organic layers were washed with brine,dried over Na2SO4, and concentrated in vacuo. The residue was purified bychromatography on silica gel, using the solvent system indicated.

The synthetic route of 29263-94-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Swift, Elizabeth C.; Williams, Theresa M.; Stephenson, Corey R. J.; Synlett; vol. 27; 5; (2016); p. 754 – 758;,
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Synthetic Route of 2876-78-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 2876-78-0, name is Methyl 1-Naphthaleneacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1): EPO In Scheme (1), compound 2 was prepared from compound 1 in 33% yield according to reference paper “J. Amer. Chem. Soc, 1935, 57, 1658-1659”, the relevant teachings of which are incorporated herein by reference. Conversion of compound 2 in the presence of dimethyl sulphate and potassium carbonate in acetone gave compound 3 in 96% yield after chromatography on silica gel. Compound 4 was prepared by coupling of compound 3 with methyl naphthalene acetate using sodium methoxide as base. The isolation yield is 29%. Proton NMR of compound 4 indicated equilibrium between /3-keto and enolate.Compound 4 (90 mg) was treated with BBr3 (20 equiv.) in DCM. Purification of the crude by chromatography gave compound 5 as pink solid (46 mg).Preparation of compound 6 was conducted using compound 5 (30 mg) in the presence of 0.20 mL of hydrazine (45 equiv) in DME (2 mL) at reflux 2 hours. Chromatography of the crude product gave compound 6 as a light purple solid (25 mg, 74% yield). 1H-NMR (Acetone-d6) delta (ppm): 7.89 (t, J=7.8Hz, 2H), 7.74 (d, J=7.8Hz, IH), 7.3-7.5 (m, 4H), 6.42 (s, IH), 6.34(s, IH), 1.9 (m, 2H), 0.32 (t, J=7.5Hz, 2H); ESMS calcd. for C21H18N2O3: 346.1; Found: 347.6 (M+l)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 1-Naphthaleneacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNTA PHARMACEUTICALS CORP.; WO2007/21966; (2007); A1;,
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Application of 179022-43-6, The chemical industry reduces the impact on the environment during synthesis 179022-43-6, name is Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, I believe this compound will play a more active role in future production and life.

Example 3: 8- [7-(cis-4-methyl-cyclohexyloxy)-8-trifluoromethyl-naphthalen-2-ylmethyl]-8-aza-bicyc lo[3.2.1]octane-3-carboxylic acid To a solution of methanesulfonic acid 7- (cis-4-methyl-cyclohexyloxy)-8-trifluoromethyl-naphthalen-2-ylmethyl ester (105 mg, 0.252 mmol) in N,N-dimethylformamide (2.9 mL, 38 mmol), 8- aza-bicyclo[3.2.1]octane-3-carboxylic acid methyl ester; HC1 salt (103.72 mg, 0.50426 mmol) was added, followed by cesium carbonate (246.44 mg, 0.75638 mmol). The reaction was then heated at 80 C for lh. LCMS showed no SM left, and the completion of the reaction (RT 1.56 min.; MH+ 490.3 and 1.49 min, 476.30. Cooled down, the reaction mixture was diluted with EtOAc, washed with water (2x). The organic phase was then separated, dried and concentrated. The crude was purified by HPLC, removed the solvent, the ester was then dissolved in tetrahydrofuran (1.2 mL, 14 mmol) , treated with 1.0 M of lithium hydroxide in water(1.8 mL, 1.8 mmol) at rt overnight. Acidified with conc.HCl, the organic layer was dried and concentrated. The crude was then purified by HLPC to give the title compound as a white powder (57.6 mg, 48%). LCMS: RT = 1.49 min.; MH+ 476.20; 1H NMR (400 MHz, METHANOL-d4) delta 8.36 (s, 1H), 8.15 (d, J = 9.29 Hz, 1H), 8.04 (d, J = 8.34 Hz, 1H), 7.61 (d, J = 9.54 Hz, 1H), 7.57 (d, J = 6.78 Hz, 1H), 4.96 (br. s., 1H), 4.41 (s, 2H), 4.02 (br. s., 2H), 2.81 – 3.09 (m, 2H), 1.44 – 2.63 (m, 16H), 0.98 (d, J = 5.84 Hz, 3H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 8-azabicyclo[3.2.1]octane-3-carboxylate hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOGEN IDEC MA INC.; GUCKIAN, Kevin; KUMARAVEL, Gnanasambandam; MA, Bin; MI, Sha; PENG, Hairuo; SHAO, Zhaohui; SUN, Lihong; TAVERAS, Arthur; WANG, Deping; XIN, Zhili; ZHANG, Lei; WO2014/18881; (2014); 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. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, A new synthetic method of this compound is introduced below., Product Details of 148547-19-7

To methyl 4-bromo-3 -methyl benzoate (92 g, 0.402 mol), (4-methoxyphenyl)boronic acid (61.1 g, 0.402 mol), Na2CO3 (85.2 g, 0.804 mol), and PdCl2(PPh3)2 (1410 mg, 2.01 mmol) was added EtOH (1.23 L) and water (0.61 L). The reaction was then heated to 80 0C for 1 hour. The reaction was cooled to room temperature, 550 ml of water was added, and the mixture was left standing for 1 hour. The resulting solids were filtered and washed with a solution of EtOH and H2O (1:1, 75O mL). The solids were ground using a mortar and pestle, then were slurried in 250 mL H2O at room temperature for 1 h, then were filtered and washed with water (2×125 mL), and were dried to give methyl 4′-methoxy-2- methylbiphenyl-4-carboxylate. IH NMR (CDCl3, 400 MHz) delta 7.95 (s, IH), 7.89 (d, J = 7.9 Hz, IH), 7.29 (d, J = 7.9 Hz, IH), 7.27 (d, J = 8.7 Hz, 2H), 6.98 (d, J = 8.7 Hz, 2H), 3.94 (s, 3H), 3.87 (s, 3H), 2.33 (s, 3H).

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:
Patent; MERCK & CO., INC.; WO2007/41494; (2007); A2;,
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