Esters-buliding-blocks

Reference of 17100-65-1, 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 17100-65-1 as follows.

[0162] Step c: To a reaction vial containing 7-amino-4-chloro-isoindolin-l-one (250 mg, 1.37 mmol) in dioxane (10 mL) was added methyl 2-bromo-5-methoxy-benzoate (502 mg, 2.05 mmol), cesium carbonate (893 mg, 2.74 mmol), copper iodide (104 mg, 0.55 mmol) and (1S,2S)- Nl,N2-dimethylcyclohexane-l,2-diamine (156 mg, 1.1 mmol). The mixture was purged with nitrogen, then warmed to 110 C. The reaction was stirred at 110 C for lh and the reaction was monitored by LC-MS. Following completion, the reaction was allowed to cool and was then filtered through Celite and rinsed with ethyl acetate. The crude was purified by silica gel chromatography (0-50% ethyl acetate/hexane) to give methyl 2-(7-amino-4-chloro-l-oxo- isoindolin-2-yl)-5-methoxy-benzoate. MS: (ES) m/z calculated for CI7HI5C1N204[M+H]+347.1, found 347.1.

According to the analysis of related databases, 17100-65-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; LELETI, Manmohan, Reddy; MALATHONG, Viengkham; MCMAHON, Jeffrey; TANKAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; MALI, Venkat; (104 pag.)WO2017/87610; (2017); A1;,
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Reference of 125568-73-2,Some common heterocyclic compound, 125568-73-2, name is Methyl 5-amino-2,4-difluorobenzoate, molecular formula is C8H7F2NO2, 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 of methyl 5-amiotano-2,4-diotafluorobenzoate intermediate 19 (5 5 g, 29 5 mmol, 1 equiv) in dichloromethane (100 mL) at -40 0C was treated with pyridine (7 16 mL, 88 6 mmol, 3 0 equiv) and 1 9 M phosgene in toluene (23 3 mL, 44 3 mmol, 1 5 equiv) After 1 5 h, a solution of 1 ,1-diotamethylethyl 4-(butylamiotano)-1-piotaperiotadiotanecarboxylate intermediate 20 (9 1 g, 35 4 mmol, 1 2 equiv) in dichloromethane (50 mL) was added and the reaction was allowed to warm to RT for 18 h The reaction was diluted with dichloromethane, washed with satd aq NaHCO3, dried over Na2SO4, filtered and concentrated to give intermediate 21 (13 1 g, 95% yield) a white solid1H NMR (400 MHz, DMSO-cfe) delta ppm 8 09 (s, 1 H), 7 89 – 7 99 (m, 1 H), 7 42 (t, J=10 62 Hz, 1 H), 3 88 – 3 99 (m, 1 H), 3 85 (s, 3 H), 3 11 – 3 22 (m, 2 H), 2 96 (d, J=12 27 Hz, 2 H), 2 41 – 2 53 (m, 3 H), 1 43 – 1 59 (m, 5 H), 1 21 – 1 35 (m, 2 H), 1 20 (s, 9 H), 0 90 (t, J=I 33 Hz, 3 H) ES-LCMS m/z 468 1 (M-H); Intermediate 291 ,1-diotamethylethyl 4-[[({2,4-diotafluoro-5-[(methyloxy)carbonyl]phenyl}amiotano)carbonyl](3- fluorophenyl)amiotano]-1-piotaperiotadiotanecarboxylateA solution of methyl 5-amiotano-2,4-diotafluorobenzoate intermediate 19 (5 O g, 26 5 mmol, 1 equiv) in dichloromethane (150 mL) at -40 0C was treated with pyridine (6 4 mL, 79 7 mmol, 3 0 equiv) and 1 9 M phosgene in toluene (20 1 mL, 39 8 mmol, 1 5 equiv) After 1 5 h, the reaction was concentrated down and dried under vac The residue was taken up in dichloromethane (150 mL) and 1 ,1-diotamethylethyl 4-[(3-fluorophenyl)amiotano]-1- piperidmecarboxylate intermediate 6 (8 6 g, 29 2 mmol, 1 1 equiv) was added and the reaction was heated to 40 0C 18 h The reaction was diluted with dichloromethane, washed with satd aq NaHCO3, dried over Na2SO4, filtered and concentrated The residue was purified by silica gel flash column chromatography (0 ? 30% ethyl acetate hexanes) to give intermediate 29 (12 6 g, 94% yield) a white solid1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8 65 (dd, J=8 88, 7 78 Hz, 1 H), 744 – 7 55 (m, 1 H), 7 17 – 7 24 (m, 1 H), 7 04 (d, J=I 87 Hz, 1 H), 6 92 – 6 99 (m, 1 H), 6 80 (t, J=10 26 Hz, 1 H), 5 96 (d, J=Z 11 Hz, 1 H), 4 56 – 4 70 (m, 1 H), 4 03 – 4 26 (m, 2 H), 3 80 – 3 92 (m, 3 H), 2 79 (s, 2 H), 1 85 (d, J=13 37 Hz, 2 H), 1 39 (s, 9 H), 1 19 – 1 35 (m, 2 H) ES-LCMS m/z 530 1 (M+Na)

The synthetic route of 125568-73-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/75960; (2009); A1;,
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Synthetic Route of 91367-05-4,Some common heterocyclic compound, 91367-05-4, name is Methyl 4-chloro-3-methylbenzoate, molecular formula is C9H9ClO2, 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 methyl 4-chloro-3-methylbenzoate (5.0 g, 27.0 mmol) in THF (30 ml.) at 00C, LHMDS (1.0 M in THF, 57 ml_, 57 mmol) was added and the solution was allowed to stir for 5 min. A solution of 2-chloro-4-methylpyrimidine (3.47 g, 27.0 mmol) dissolved in THF (8 ml.) was added dropwise at 00C and the reaction mixture was allowed to stir for 30 min. The reaction mixture was quenched at 00C with MeOH (50 ml.) and the solvent was removed in vacuo. The residue was diluted with EtOAc and washed with water. The organic layer was dried over MgSO4, filtered and evaporated. The title compound of Step A was purified by trituration with EtOAc. The title compound of Step A was obtained as a solid in 20% yield (1.5 g). MS (APCI): 281.1 [M+H]+.

The synthetic route of 91367-05-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/32667; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 185312-82-7, name is Methyl 4-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H6BrClO2

To a stirred solution of 4-bromo-2-chlorobenzoic acid, methyl ester (18.69 g) in triethylamine (110 ml), was added 1-dimethylamino-2-propyne (12.1 ml), bis(triphenylphosphine)palladium(II) chloride (1.26 g), and copper(I) iodide (0.136 g). The mixture was heated slowly to 60 C., and the temperature maintained for one hour. The reaction was cooled to room temperature, filtered through diatomaceous earth, and the collected solid washed with ethyl acetate. The solvent was removed in vacuo, the resulting residue redissolved in ethyl acetate, and washed with water (3¡Á). The combined organic extract was dried over anhydrous sodium sulfate, and the solvent removed in vacuo to give a crude product. The crude product was purified by column chromatography on silica gel (225 g), eluting with 40% ethyl acetate/hexane. After removing the solvent in vacuo, the title compound was obtained as a viscous oil (17.7 g), MS (+FAB), m/z: 252 (M+H)+.

The synthetic route of 185312-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 927-68-4, A common heterocyclic compound, 927-68-4, name is 2-Bromoethyl acetate, molecular formula is C4H7BrO2, 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.

To a 250 mL flask equipped with magnetic stirring bar, 1-(3-fluoro-2-nitrophenyl)piperazine A-6 (5 g, 22.5 mmol) was added under argon atmosphere and the flask was filled with dry ACN (50 mL). Then, dried K2CO3 (6,0 g, 45 mmol) and 2-bromoethyl acetate (4.45 g, 26.6 mmol) were added, and the reaction mixture was heated to 60 C and stirred for 20h at this temperature. After this time UPLCMS analysis showed no substrate peak. The reaction was cooled to room temperature and solid was filtered. As a result, the product A-2C was obtained as the yellow solid (6.8 g, 99% yield) with 99 % of purity, according to UPLCMS analysis (Method A).

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; Adamed sp. z o.o.; KOLACZKOWSKI, Marcin; BUCKI, Adam; SNIECIKOWSKA, Joanna; MARCINKOWSKA, Monika; (65 pag.)EP3530651; (2019); A1;,
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Related Products of 369-25-5,Some common heterocyclic compound, 369-25-5, name is Methyl 3,4-difluorobenzoate, molecular formula is C8H6F2O2, 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.

Intermediate 9: Methyl 4-{(3S)-aminopiperidin-1-yl}-3-fluorobenzoate N -Methylpyrrolidone (40 ml) was added to methyl 3,4-difluorobenzoate (1.29 g, 7.5 mmol), and the mixture was stirred at room temperature. Intermediate 8 (2.6 g, 15.0 mmol) and sodium hydrogencarbonate (4.03 g, 48 mmol) were added thereto, and the mixture was stirred at 110C overnight. Water (70 ml) was added to thereaction solution, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (development system: chloroform: methanol = 8: 2) to give the title compound (0.55 g, 29%).

The synthetic route of 369-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meiji Seika Kaisha, Ltd.; EP1227083; (2002); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 91-44-1, A common heterocyclic compound, 91-44-1, name is 7-(Diethylamino)-4-methyl-2H-chromen-2-one, molecular formula is C14H17NO2, 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.

To a 25 mL reaction tube, add Na2CO3 (63.6 mg, 0.60 mmol), 69.4 mg (0.30 mmol, 1 equivalent) of compound C-2,After replacing with argon three times, 1 mL of acetone (Acetone) + 1 mL of N, N-methylformamide (DMF) was added.After injecting 132 muL (0.90 mmol) of compound E-1 and stirring under blue light for 24 hours, compound H-2 was obtained with a yield of 95%.

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; Zunyi Medical University; He Chunyang; Mao Ting; Zhao Liang; Li Xiaofei; (13 pag.)CN110642831; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 107317-58-8, 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 107317-58-8 as follows.

To a solution of methyl 4-bromo-3-(trifluoromethyl)benzoate (10 g, 35.33 mmol) in THF (100 mL) under nitrogen was added 2 M lithium borohydride in THF (2.309 g, 106.0 mmol). The mixture was heated at reflux. The mixture was cooled to 0C and carefully quenched with 6 N HC1 (aq) (about 20 mL or less) (vigorous in the beginning 3-5 mL) up to pH 3. The mixture was diluted with water (25 mL) and extracted with EtOAc (2X). The combined organics were dried over anhydrous Na2S04and filtered. The filtrate was concentrated in vacuo to dryness to afford the crude (4-bromo-3- (trifluoromethyl)phenyl)methanol as a brown solid.

According to the analysis of related databases, 107317-58-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; SADEQUE, Abu J.M.; BUZARD, Daniel J.; (82 pag.)WO2020/51378; (2020); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 52273-79-7, name is Ethyl 2-(3-aminophenyl)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. Formula: C10H13NO2

(3-Amino-phenyl)-acetic acid ethyl ester (0.895 g, 5.0 mmol) and acetyl chloride (0.26 mL, 5.0 mmol) are added to a round bottomed flask containing THF (20 mL), pyridine (0.60 mL) and DMAP (10 mg). The mixture is stirred at room temperature overnight. The clear solution is diluted with EtOAc (200 mL), washed with 1N HCl (3¡Á100 mL) and brine (100 mL), and dried with MgSO4. Solvent is evaporated in vacuo to afford intermediate 14-B as a white solid that is used without further purification

The synthetic route of Ethyl 2-(3-aminophenyl)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; US2007/276002; (2007); A1;,
Ester – Wikipedia,
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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 4630-82-4 as follows. Computed Properties of C8H14O2

Example 5; Catalytic hydrogenation of various esters using complex [RuCyT?-BINAP)(S,S-DPEN)]; General procedure for the catalytic hydrogenation of methyl benzoate as substrate: Under argon, a Keim autoclave was charged with [RuCl2(i?-BINAP)(dmf)2] (0.01 mmol, 0.05 mol%) and S5S-DPEN (0.01 mmol, 0.05 mol%) followed by THF (2 ml) and the solution stirred for 5 minutes. Then a solution of the desired ester (20 mmol) in THF (2 ml), followed by more THF (2 x 1 ml), and a solution of tridecane (1 mmol) in THF (2 ml), as internal standard, followed by more THF (2 x 1 ml), were successively added to the autoclave. Finally, solid NaOMe (1 mmol, 5 mol%) was added and the autoclave was pressurised with hydrogen gas at 50 bars and placed in a thermostatted oil bath set at 600C. After the mentioned time, the autoclave was removed from the oil bath, and cooled in a cold-water bath. Then, an aliquot (0.4 ml) was taken, diluted with MTBE (5 ml), washed with aq. sat. NH4Cl (5 ml), and filtered over a plug of celite and analyzed by GC.Table 5 : Hydrogenation of various esters using complex [RuCl^-BINAPX^S-DPEN)]Com/Base: molar ratio in ppm relative to the substrate of complex and base. GC: percent of product analysed by GC in the crude reaction mixture. Reaction conditions: H2 gas (50 bars), 600C, NaOMe as base and THF (2 M).

According to the analysis of related databases, 4630-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FIRMENICH SA; WO2008/65588; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics