Tag: M.W=100-200

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. 4606-07-9, name is Ethyl cyclopropanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl cyclopropanecarboxylate

General procedure: To a three-necked, 50 mL flaskequipped with a magnetic stirring bar, 15 mL of THF, 2.5 mmol of ester (1 equiv), 0.375 mmol of CuO (15% equiv), 7.5 mmol of aryl halides and magnesium chips (3 equiv) or 15 mmol of alkyl bromides and magnesium chips (6 equiv) were added. The reaction mixture was heated at 65 C for 4 h. The progress of the reaction was monitored by TLC. Then, the reaction was quenched by saturated aqueous NH4Cl (5 mL), extracted with AcOEt (10 mL × 3), dried over sodium sulfate, filtered, and evaporated to give the raw product. Pure product could be obtained by TLC with petroleum /AcOEt = 5/1 as eluent.

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; Gao, Fei; Deng, Xiang-Jun; Tang, Yu; Tang, Jin-Peng; Yang, Jun; Zhang, Yuan-Ming; Tetrahedron Letters; vol. 55; 4; (2014); p. 880 – 883;,
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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. 4492-02-8, name is Ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., name: Ethyl 4,5,6,7-tetrahydro-1H-indazole-3-carboxylate

Preparation 5 Indazole-3-Carboxylic Acid A mixture of 4,5,6,7-tetrahydroindazole-3-carboxylic acid ethyl ester (21.0 g, 108 mmol), 5% palladium on carbon (7.0 g solid, 3.29 mmol of Pd), and 210 mL of cymene was heated to reflux for 38 hours. At this point complete conversion to the indazole-3-carboxylic acid ethyl ester was shown by TLC (silica gel, 3:1 ethyl acetate-heptane). The reaction was cooled to 120 C. and the 5% palladium on carbon was removed by filtration.

According to the analysis of related databases, 4492-02-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Eli Lilly and Company; US6069152; (2000); A;,
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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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., category: esters-buliding-blocks

2-Methoxy-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid (131 mg, 557 mumol) was suspended in DMF (1.70 mL). Methyl 3-amino-4-chlorobenzoate (155 mg, 835 mumol) was added, followed by triethylamine (283 mg, 390 muL, 2.8 mmol). HATU (318 mg, 835 mumol) was then added. Solution was initially clear but solid soon began to precipitate out of solution. After stirring at room temperature for 16 hours the reaction mixture was diluted with EtOAc (1 mL). The solid was then collected by filtration, washed with EtOAc and dried to give methyl 4-chloro-3-(2-methoxy-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamido)-benzoate. (Yield 108 mg, 244 mumol, 43.8%).

According to the analysis of related databases, 40872-87-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Anderson, Kevin; Chen, Yi; Chen, Zhi; Luk, Kin-Chun; Rossman, Pamela Loreen; Sun, Hongmao; Wovkulich, Peter Michael; US2012/184542; (2012); A1;,
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Synthetic Route of 15963-46-9, These common heterocyclic compound, 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, 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 solution of 8-chloro-N-(4-chloro-2-hydroxyphenyl)-4-oxo-chromene-2-carboxamide (190 mg, 543 m mol), methyl 3-chlorocyclobutane-l-carboxylate (105 mg, 75 m L, 543 mmol) in DMF (5 mL) was added CS2CO3 (260 mg, 782 miho) at room temperature and the resulting mixture was then stirred at 90 C for 12 hours. After the reaction was completed, the mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL) three times. The combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated in vacuo to give methyl 3-(5-chloro-2-(8-chloro-4-oxo-chromene-2-carboxamido)phenoxy)cyclobutane- 1- carboxylate (200 mg, 79.8 %) as a yellow foam, which was used in next step directly without further purification. MS obsd. (ESL) [(M+H)+]: 462.1.

The synthetic route of 15963-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; FENG, Song; LIANG, Chungen; LIU, Yongfu; TAN, Xuefei; WU, Jun; WANG, Jianping; (134 pag.)WO2020/79106; (2020); 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. 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-amino-4-methylbenzoate

2.47 g (34.5 mmol) of sodium nitrite was dissolved in 3.8 ml of water, and it was added dropwise to a mixture of 5.64 g (34.1 mmol) of methyl 3-amino-4-methyl-benzoate and 140 ml of acetic acid under ice-cooling. After the temperature of the reaction mixture was allowed to warm to room temperature and the mixture was stirred overnight, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over magnesium sulfate and filtered. The solvent was distilled off to give 4.83 g (yield: 80%) of methyl indazole-6-carboxylate. MASS(ESI+) m/z= 177 (M+H)+

The synthetic route of 18595-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nissan Chemical Industries, Ltd.; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP2045253; (2009); A1;,
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Application of 13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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.

Hexamethylphosphoric triamide (10.7 g, 59.9 mmol) was dissolved in tetrahydrofuran (160 mL) under nitrogen(0.5 M, 36 mL) was added at 0 C for 0.5 hour at 0 C, tert-butyl propiolate (5.04 g, 40 mmol) was added and the reaction was continued for 1 hour. Then add 2b (5.47g, 40mmol), gradually rose to room temperature, reaction 5 hours, slowly adding 1M hydrochloric acid to the reaction solution, adjust the reaction solution pH to 2 ~ 3, The organic phase was washed with saturated brine (100 mL x 1), dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography and purified. The organic phase was extracted with ethyl acetate (50 mL x 2) (Ethyl acetate: petroleum ether (v / v) = 0: 1 to 1: 9) to give the title compound 2c as a yellow oil (2.2 g, yield 21%).

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

Reference:
Patent; Sichuan Hai Sike Pharmaceutical Co., Ltd.; Wei Yonggang; Qiu Guanpeng; Lei Bolin; Li Yao; Wang Song; Zhu Guozhi; (39 pag.)CN106279128; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 884497-46-5, name is Methyl 3-amino-5-fluorobenzoate, 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 884497-46-5, Computed Properties of C8H8FNO2

Step C. Methyl 3-(dibenzylamino)-5-fluorobenzoate. To a solution of methyl 3-amino-5- fluorobenzoate (440 mg, 2.6 mmol) in dry DMF ( 10 mL) was added NaH ( 1 87 mg, 7.8 mmol) portionwise, followed by addition of benzyl bromide (1 . 1 g, 6.5 mmol). The reaction mixture was stirred at 40 C for 16 hr and concentrated. The resulting residue was purified by column chromatography to give the desired product. MS: 350 (M+ l )+.

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Reference:
Patent; AGIOS PHARMACEUTICALS, INC.; LEMIEUX, Rene M.; POPOVICI-MULLER, Janeta; TRAVINS, Jeremy M.; CAI, Zhenwei; CUI, Dawei; ZHOU, Ding; WO2015/10297; (2015); A1;,
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Electric Literature of 4630-80-2,Some common heterocyclic compound, 4630-80-2, name is Methyl cyclopentanecarboxylate, molecular formula is C7H12O2, 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.

EXAMPLE 61 120N-(5-(l-piperazinyl)-2-pyridinyl)spiro[cyclopentane-l,9′- pyrido [4′,3′ :3,4] cyclopenta[l,2-d] pyrimidin]-2′-amine 1212-(3-Bromo-4-pyridinyl)-l-cyclopentylethanone (121) Under a nitrogen atmosphere LiHMDS (LOM solution in tetrahydrofuran, 49.6 ml, 49.6 mmol) was added to a solution of methyl cyclopentanecarboxylate (3.630 g, 28.3 mmol) and 3-bromo-4-methylpyridine (2.62 ml, 23.6 mmol) in 10ml of anhydrous THF over a period of 5min at -780C. AfterlOmin the solution was allowed to warm to 2O0C and stirred for 2hours. The solution was then cooled in ice water, before the pH was adjusted to 4.5 with 25% citric acid. After extraction with DCM the organic layer was dried over Na2SO4 and then concentrated to afford 2-(3-bromo-4-pyridinyl)-l-cyclopentylethanone (121) (6.86g, crude). 1H NMR (500 MHz, DMSO-d6) delta 8.68 (IH, s), 8.48 (IH, d, J = 4.9Hz), 7.37 (H, d, J = 4.9 Hz), 4.07 (2H, s), 3.08 (IH, ddd, Jl = 16.1 Hz, J2 = 7.3 Hz, J3 = 1.2 Hz), 1.80- 1.85 (2H, m), 1.72-1.77 (2H, m), 1.55-1.59 (4H, m); LCMS-ESI (POS), M/Z, M+l : Found 268.0

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

Reference:
Patent; AMGEN INC.; WO2009/126584; (2009); A1;,
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Synthetic Route of 2150-38-1, A common heterocyclic compound, 2150-38-1, name is Methyl 3,4-dimethoxybenzoate, molecular formula is C10H12O4, 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.

(1) Preparation of 3,4-dimethoxybenzoylacetonitrile Dry acetonitrile (1.8 ml) was added to a solution of n-butyllithium (a 2.5M hexane solution, 13.8 ml) in dry THF (30 ml) at -78 C., and the mixture was stirred at the same temperature for 1 hour. To the mixture was added a solution of methyl 3,4-dimethoxybenzoate (6.42 g) in dry THF (15 ml) and the mixture was stirred at -78 C. for 3 hours and then at room temperature for 1 hour. Water (100 ml) was added to the reaction solution which was subsequently extracted with ethyl ether (100 ml). After the aqueous layer was acidified with 6 N hydrochloric acid, it was extracted with ethyl acetate (200 ml*3). The oragnic layers were combined, washed with saturated brine and then dried over anhydrous sodium sulfate. Then, the solvent was distilled away under a reduced pressure. The resultant residue was crystallized from ethyl acetate-hexane to obtain the title compound (3.6 g) as pale yellow crystals. 1H-NMR (CDCl3)delta: 3.95 (3H, s), 3.97 (3H, s), 4.03 (2H, s), 6.92 (1H, d, J=9.0 Hz), 7.49 (1H, d, J=9.0 Hz), 7.51 (1H, s)

The synthetic route of 2150-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Banyu Pharmaceutical Co., Ltd.; US6180653; (2001); B2;,
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. 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

To a solution of 4-(adamantan-1-yl)phenol(0.8 g, 3.50 mmol) in N,N-dimethylformamide(8 mL) was added anhydrous potassium carbonate(1.45 g, 10.51 mmol) and methyl 2-bromo-2-methylpropanoate(1.15 g, 7.0 mmol), and stirred at room temperature for 12 hours. The reaction mixture was diluted with ethyl acetate and washed with aqueous sodium bicarbonate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was filtered and evaporated under reduced pressure to afford a crude solid, which was purified by silica gel column chromatography to give methyl 2-(4-(adamantan-1-yl)phenoxy)-2-methylpropanoate as colorless oil(1.1 g, 94.1% yield). [288] 1H-NMR (MeOH-d4, 500 MHz) delta 7.21 (2H, d, aromatic-H), 6.75 (2H, d, aromatic-H), 3.73 (3H, s, OCH3), 2.05 (3H, brs, adamantyl-H), 1.88 (6H, m, adamantyl-H), 1.77 (6H, m, adamantyl-H), 1.52 (6H, s, (CH3)2).

The synthetic route of 23426-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DONGGUK UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; LEE, Kyeong; WON, Mi-Sun; KIM, Hwan-Mook; PARK, Song-Kyu; LEE, Ki-Ho; LEE, Chang-Woo; KIM, Bo-Kyung; BAN, Hyun-Seung; CHUNG, Kyung-Sook; RAVI, Naik; CHOI, Hyun-Kyung; WO2013/48164; (2013); A1;,
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