Month: September 2021

Some common heterocyclic compound, 25415-67-2, name is Ethyl 4-methylpentanoate, molecular formula is C8H16O2, 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: C8H16O2

EXAMPLE 37 (FROM TABLE 1) 5-Bromo-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic Acid (3-diethylaminopropyl)amide A mixture of 2-aminoacetophenone hydrochloride (1 equiv.), ethyl isobutylacetate (1.2 equiv.) and sodium acetate (2.4 equiv.) in H2O was stirred at 100 C. for 18 hours and then cooled to room temperature. The aqueous layer was decanted off and the oil was dissolved in ethyl acetate. It was then washed with water and brine and then dried to give (93%) of 2-isopropyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester as a red brown oil. 1H NMR (300 MHz, DMSO-d6) delta 11.21 (s, br, 1H, NH), 7.14-7.27 (m, 5H), 6.70 (d, J=2.7 Hz, 1H), 4.02 (q, J=7.1 Hz, 2H, OCH2CH3), 3.65 (m, 1H, CH(CH3)2), 1.22 (d, J=7.5 Hz, 6H, CH(CH3)2), 1.04 (t, J=7.1 Hz, 3H, OCH2CH3). MS-EI m/z 257 [M+].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 25415-67-2, its application will become more common.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 34837-84-8, 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. 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5A. Methyl 2-(4-fluorophenyl)-3-(4-(methylsulphonyl)phenyl)-3-oxopropanoate A solution of methyl 2-(4-fluorophenyl)acetate (2.35 g, 14 mmol) in THF (15 mL), at -78° C., was treated dropwise with 1 N lithium bis(trimethylsilyl)amide (14 mL, 14 mmol). After 15 minutes a suspension of 4-(methylsulphonyl)benzoyl chloride (3.3 g, 15 mmol) in THF (25 mL) was added in portions. The reaction mixture was stirred for 60 minutes at -78° C. and at 0 to 5° C. for 12 hours. The mixture was quenched with 10percent citric acid, the THF removed in vacuo, and the residue triturated with hexanes to provide the desired product as a solid (yield: 3.4 g; 69percent). MS (DCI-NH3) m/z 368 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta3.27 (s, 3H), 3.69 (s, 3H), 6.35 (s, 1H), 7.21 (m, 2H), 7.44 (m, 2H), 8.06 (d, J=9 Hz, 2H), 8.25 (d, J=9 Hz, 2H).

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 2-(4-fluorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Abbott Laboratories; US6472416; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 27798-60-3, 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 27798-60-3 as follows.

Example 7a 3-(2,4-Dichloro-pyrimidin-5-yl)-2-(2-methoxy-phenyl)-propionic acid methyl ester To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 ML) was added n-butyllithium (2.5 M in hexanes, 4.0 ML, 10.0 mmol) (Aldrich) at -78 C. under argon.After 30 minutes, a solution of 2-methoxyphenylacetic acid methyl ester (1.8 g, 10.0 mmol) (TCI-US) in tetrahydrofuran (5 ML) was added by injection via a syringe and the reaction mixture was stirred at -78 C. for another 30 minutes.To the reaction mixture was added a solution of 2,4-dichloro-5-iodomethyl-pyrimidine (1.45 g, 5.0 mmol) (from Example 1c supra) in tetrahydrofuran (5 ML) at -78 C. and the reaction mixture was stirred at the same temperature for 1 hour then slowly allowed to warm up to -30 C. and stirred for 10 minutes.The reaction mixture was diluted with ethyl acetate (100 ML) and successively washed with saturated aqueous ammonium chloride solution (100 ML), water (50 ML) and brine (50 ML), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo.The residue was purified by flash column chromatography to give 3-(2,4-dichloro-pyrimidin-5-yl)-2-(2-methoxy-phenyl)-propionic acid methyl ester as a yellow oil. (Yield 1.40 g, 82.3%).

According to the analysis of related databases, 27798-60-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Jin-Jun; Luk, Kin-Chun; US2004/122029; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 29263-94-3, 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 29263-94-3 as follows.

A. To a solution of 2-amino-5-nitrophenol (6.00 g, 0.0326 mol) in 80 mL of DMF was added diethyl 2-bromo-2-methyl malonate (6.2 mL, 0.0326 mol) and potassium fluoride (4.74 g, 0.0815 mol). The reaction mixture was heated at 60 C. for 6 hours. Water was added to quench the reaction and the reaction mixture was extracted with EtOAc. The combined organic fractions were dried over MgSO4, filtered and the filtrate was concentrated to dryness. The residue was purified by chromatography (silica with hexanes and ethyl acetate) to afford 2-methyl-6-nitro-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester.

According to the analysis of related databases, 29263-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Calvo, Raul R.; Cheung, Wing S.; Player, Mark R.; US2006/116368; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 394-35-4 as follows. name: Methyl 2-fluorobenzoate

0.06 mol of methyl o-fluorobenzoate,0.022 mol DIC,6.6 mmol DMAP was added to 100 mL dichloromethane, Stirring to continue stirring at room temperature for 30min,Gradually warming to 45 ~ 50 ,The reaction flask was charged with 1-cyclopropanecarbonylpiperazine (0.08 mol)Continue stirring reaction 9 ~ 10h.After the reaction is completed,Cool to 0 C and stir 45min,filter,The filtrate was washed with water (3 * 50 mL)Dried over anhydrous sodium sulfate,The methylene chloride was evaporated under reduced pressure,Got solid,Compound 2 (15.27 g),The yield is 92.57%.

According to the analysis of related databases, 394-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Yuxin Pharmaceutical Co., Ltd.; Liu Zhenteng; Sun Yiwei; Li Zhen; Xu Guichao; Leng Xiangxiang; Huang Chunyan; (9 pag.)CN107266370; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 1459-93-4 as follows. Safety of Dimethyl isophthalate

In a round bottom flask was added dimethyl terephthalate, 0.07mol substituted and 150 mL of methanol, add 100mL of hydrazine hydrate, refluxed for 24 hours, cooled to room temperature for 5 hours and filtered, washed with water, and dried to give phthalimido-substituted hydrazide.

According to the analysis of related databases, 1459-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangxi Tianyuan biochemistry Co.Ltd; Zhang, Qing; Li, Weiguo; Li, Xianling; (15 pag.)CN103864711; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, name is tert-Butyl 4-bromobenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C11H13BrO2

(2S,3’S)-2-Methyl-[1,3′]bipyrrolidinyl dihydrochloride (8) (1.1 g, 4 mmol) was treated with NaOt-Bu (1.1 g, 2equiv) in MeOH (30 mL), filtered, and concentrated. To this flask was added tert-butyl-4-bromo-benzoate (9) (1.0 g, 3.89 mmol), sodium tert-butoxide (538 mg, 5.6 mmol), tris(dibenzylideneacetone)-dipalladium-(0) (35 mg, 0.039 mmol), BINAP (72 mg, 0.116 mmol), and toluene (40 mL) under nitrogen. The reaction flask was heated to 80 °C (external) for 24 h with stirring until the starting material was completely consumed as judged by TLC analysis. The mixture was cooled to room temperature, taken up in DCM (50 mL), filtered, and concentrated. The crude product was then purified by a silica gel flash chromatography eluted with 0-5percent of 7 N NH3/MeOH in DCM to get 1.02 g (80percent) of the title compound as a yellow oil. LCMS: RT = 2.23 min, MS: 331 (M+H+). 1H NMR (300 MHz, CDCl3) delta 7.87 (d, J = 8.7 Hz, 2H), 6.49 (d, J = 8.7 Hz, 2H), 3.6-3.23 (m, 5H), 3.01 (m, 1H), 2.78 (m, 1H), 2.55 (q, J = 8.4 Hz, 1H), 2.22-1.43 (m, 13H), 1.14 (d, J = 6.3 Hz, 3H).

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gao, Zhongli; Hurst, William J.; Hall, Daniel; Hartung, Ryan; Reynolds, William; Kang, Jiesheng; Nagorny, Raisa; Hendrix, James A.; George, Pascal G.; Bioorganic and Medicinal Chemistry; vol. 23; 3; (2015); p. 429 – 438;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of Methyl 3-amino-4-methoxybenzoate

Preparation of the compound of formula VII :; To a solution of METHYL-3-AMINO-4-METHOXYBENZOATE (a compound of FORMULA 11, AVAILABLE FROM INDOFINE CHEMICAL Company, INC., Somerset, New Jersey), (315 g, 1.74 mol) in 1 L MEOH, the crude enone VI (350 g,-2. 09 mol) was added. The reaction was stirred at room temperature for 30 minutes. After cooling to 0C for 1 hour, the solid was filtered and dried under vacuum to give the desired compound of formula Vil, methyl 4-methoxy-3- {[(E)-4-trifluoromethyl-3-oxo-1-butenyl] amino} benzoate, (500 g, 95% yield) as a yellow solid. 1H NMR (400 MHz, CDCI3) a 3.94 (s, 3H), 4.04 (s, 3H), 5.74 (d, J=8.0 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 7.79 (dd, J=13. 2,8. 0 Hz, 1H), 7.87 (dd, J=8.8, 2.0 Hz, 1 H), 7.92 (d, J=2.0 Hz, 1 H), 11.01 (br, 1 H)

The synthetic route of 24812-90-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2005/28471; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 141-12-8,Some common heterocyclic compound, 141-12-8, name is (Z)-3,7-Dimethylocta-2,6-dien-1-yl acetate, molecular formula is C12H20O2, 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.

General procedure: To a solution of the geranyl derivative (1.0 equiv) in acetonitrile(0.05 M) at 0 C, lithium bromide (2.0-2.4 equiv),4 A molecular sieves (1.0 mass equiv) and DIB (1.2-1.4 equiv) were added. After stirring for 5 min, the reaction mixture wasdiluted with EtOAc, filtered over alumina (EtOAc) and concentratedunder reduced pressure before purification by flash chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-3,7-Dimethylocta-2,6-dien-1-yl acetate, its application will become more common.

Reference:
Article; Peilleron, Laure; Grayfer, Tatyana D.; Dubois, Joelle; Dodd, Robert H.; Cariou, Kevin; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1103 – 1111;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics