Tag: M.W:200-300

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. 178876-83-0, name is Methyl 6-amino-3-bromopicolinate, the common compound, a new synthetic route is introduced below. category: pyridine-derivatives

To a solution of methyl 6-amino-3-bromopicolinate (1.00 g, 4.33 mmol, 1 eq) in ethanol (50 mL) was added sodium bicarbonate (618 mg, 7.36 mmol, 1.7 eq) and 1- chloropropan-2-one (2.47 g, 26.7 mmol, 6.2 eq). The reaction was stirred at 90 C for 12 hr. The reaction was cooled to 25 C and concentrated in vacuo. To the residue was added water (50 mL) and the aqueous phase was extracted with ethyl acetate (50 mL*3). The combined organic phases were washed with brine (50 mL*2), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by prep-TLC. Example 119A (400 mg, yield=34.3%) was obtained as a brown solid. ESI m/z 283.0 [M + 1] +.

The synthetic route of 178876-83-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHRYSALIS, INC.; GWALTNEY, Stephen; (147 pag.)WO2017/214413; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 17570-98-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 17570-98-8, name is 2-(Bromoacetyl)pyridine hydrobromide, molecular formula is C7H7Br2NO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

9(B) (S)-(3,4-Difluoro-phenyl)(3-(4-(pyridin-2-yl)-oxazol-2-yl)-piperidin-l- yl)-methanone; A solution of (S)-l-(3,4-difluoro-benzoyl)-piperidine-3-carboxylic acid amide (0.214 g, 0.8 mmol) and 2-(bromoacetyl)-pyridine hydrobromide (90 mg, 0.32 mmol) in dry N-methyl-2-pyrrolidinone (3 mL) was heated at 110C for 7 h. The reaction mixture was cooled to room temperature, ethyl acetate was added and the organic layer was washed sequentially with water (twice) and with brine (twice). The organics were dried over sodium sulphate and evaporated under reduced pressure to afford a crude oil that was purified by flash chromatography (silica gel, eluent gradient: from DCM/MeOH/NH4OH 99:1 :0.1 to DCM/MeOH/NH4OH 98:2:0.2). The solid that was recovered from this purification was purified again by flash chromatography (silica gel, eluent: DCM/MeOH/NH4OH 99:1 :0.1) to afford 8.5 mg of (S)-(3,4-difluoro- phenyl)(3-(4-(pyridin-2-yl)-oxazol-2-yl)-piperidin-l-yl)-methanone, obtained as a yellow gummy solid. Yield: 7%; LCMS (RT): 4.44 min (Method I); MS (ES+) gave m/z: 370.4 (MH+). EPO 1H-NMR (CDCl3, 328K), delta (ppm): 8.59 (ddd, IH) 8.17 (s, IH) 7.85 (ddd, IH) 7.73 (ddd, IH) 7.29-7.34 (m, IH) 7.16-7.25 (m, 3H) 4.29-4.39 (m, IH) 3.93-4.03 (m, IH) 3.53 (dd, IH) 3.27 (ddd, IH) 3.07-3.18 (m, IH) 1.83-2.06 (m, 2H) 1.68 (br. s., IH).

According to the analysis of related databases, 17570-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ADDEX PHARMA S.A.; WO2008/56259; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 1156542-30-1, name is 2-Bromo-5-fluoro-4-(trifluoromethyl)pyridine, the common compound, a new synthetic route is introduced below. Safety of 2-Bromo-5-fluoro-4-(trifluoromethyl)pyridine

To 12 ml of N,N-dimethylformamide were added 0.8 g of 2-bromo-5-fluoro-4- trifluoromethylpyridine, 1.41 g of zinc cyanide and 0.28 g of tetrakistriphenylphosphinepalladium, and the mixture was stirred at 950C for 14 hours. After allowing to cool, the reaction solution was poured into water, and the resultant solution was extracted with diethyl ether three times, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.5 g of 5- fluoro-4-trifluoromethylpyridine-2-carbonitrile. 5-Fluoro-4-trifluoromethylpyridine-2-carbonitrile1H-NMR: 7.96 (d, IH), 8.79 (s, IH)

The synthetic route of 1156542-30-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2009/66786; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.884495-00-5, name is 4-Bromo-5-fluoro-2-methoxypyridine, molecular formula is C6H5BrFNO, molecular weight is 206.01, as common compound, the synthetic route is as follows.Safety of 4-Bromo-5-fluoro-2-methoxypyridine

INTERMEDIATE 28 5-Fluoro-4-(3-iodo-lH-pyrazol-l-yl)-2-methoxypyridine To a solution of 3-iodopyrazole (0.20 g, 1.031 mmol), in DMSO (5.20 mL) was added sodium hydride (60% in oil, 0.045 g, 1.134 mmol) and stirred for 0.5 h before 4- bromo-5-fluoro-2-methoxypyridine (0.212 g, 1.031 mmol) was added. The reaction mixture was stirred at 80 C for 4 h. This was quenched by the addition of water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgS04 and concentrated in vacuo. The crude mixture was purified by flash chromatography (ISCO Combiflash, 12 g, 0-20 % EtOAc in hexanes) to give 5- fluoro-4-(3-iodo-lH-pyrazol-l-yl)-2-methoxypyridine, as a white solid. LCMS calc. = 319.96; found = 320.05 (M+H)+. NMR (500 MHz, CDC13): delta 8.13 (d, J= 2.8 Hz, 1 H); 7.97 (d, J = 1.7 Hz, 1 H); 7.37 (m, 1 H); 6.67 (d, J= 2.6 Hz, 1 H); 3.94 (t, J = 1.2 Hz, 3 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,884495-00-5, 4-Bromo-5-fluoro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; SMITH, Cameron, James; TAN, John, Qiang; ZHANG, Ting; BALKOVEC, James; GREENLEE, William, John; GUO, Liangqin; XU, Jiayi; CHEN, Yi-heng; CHEN, Yili; CHACKALAMANNIL, Samuel; HIRABAYASHI, Tomokazu; NAGASUE, Hiroshi; OGAWA, Kouki; WO2014/120346; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 960289-03-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.960289-03-6, name is 2-Bromo-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one, molecular formula is C7H6BrNOS, molecular weight is 232.1, as common compound, the synthetic route is as follows.

Preparation 9; 2-(4-Methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one; Combine 2-bromo-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (1.024 g, 4.42 mmol), 4-methoxyphenyl boronic acid (0.671 g, 4.42 mmol), Na2CO3 (0.94 g, 8.83 mmol), in water (10 mL), dimethoxyethane (75 mL) and CH3OH (50 mL). Purge with nitrogen for 5 min. Add Pd(PPh3 )4 (0.153 g, 0.1325 mmol) and reflux the resulting mixture overnight. Cool the reaction to RT and dilute with water (100 mL). Extract with EtOAc (3 x 100 L), and concentrate. Treat the residue with EtOAc (40 mL), collect the solid and wash with EtOAc (20 mL) and Et2O (2 x 20 mL) to give the title compound (0.950 g). Concentrate the filtrate and purify the resulting residue by chromatography to give additional product (0.140 g). The overall yield is 1.090 g (95%). MS/ES m/z 260.0 [M+H]+.

The chemical industry reduces the impact on the environment during synthesis 960289-03-6, I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/146759; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 850429-51-5, 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. 850429-51-5, name is Ethyl 6-amino-5-bromonicotinate. A new synthetic method of this compound is introduced below.

2.41 g of ethyl 2-amino-3-bromo-5-pyridinecarboxylate 3d in 120 mL of methanol and 2.8 g of potassium hydroxide in 40 mL of water are placed in a round-bottomed flask. The mixture is stirred with heating at 60 C. for 3 hours. The methanol is evaporated off. After cooling, 10 mL of 5N hydrochloric acid are added. The precipitate is filtered off to give 2.07 g of 6-amino-5-bromonicotinic acid.LC-MS-DAD-ELSD: 217(+) and 219(+)=(M+H)(+) Rt (min)=1.71

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,850429-51-5, its application will become more common.

Reference:
Patent; SANOFI-AVENTIS; US2011/178053; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1159820-58-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1159820-58-2, name is 5-Bromo-2-isopropylpyridine, molecular formula is C8H10BrN, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation of 2-isopropyl-5-vmyl-py?dme[0369] The title compound was prepared by following general procedure 2 5-Bromo-2- lsopropyl-py?dme (0 75 g, 3 7 mmol) was dissolved in DMF THF (3 1, 6 mL) T?butylvmyltm (1 2 mL, 4 12 mmol) and Pd(PPh3)4 (0 070 g, 0 06 mmol) was added to this solution at RT under nitrogen and was heated at 1000C for 30 mm The reaction mixture was cooled to RT and diluted with water (60 mL) and extracted with DCM (3 x 100 mL) The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure below 400C The crude was purified through column chromatography (90% DCM-Hexane in silica 100-200 mesh, Diameter of column – 5 0 cm, Height of silica – approx 5 inch) to provide 2-isopropyl-5- vmylpy?dme as a light yellow liquid (0 5 g, 90% yield)

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1159820-58-2, 5-Bromo-2-isopropylpyridine.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; HUNG, David, T.; PROTTER, Andrew, Asher; JAIN, Rajendra, Parasmal; CHAKRAVARTY, Sarvajit; GIORGETTI, Marco; WO2010/51503; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73112-16-0, 2,6-Dibromo-4-methylpyridine, 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, Product Details of 73112-16-0, blongs to pyridine-derivatives compound. Product Details of 73112-16-0

1A Preparation of 2-bromo-4-methyl-6-(3-trifluoromethyl-1H-pyrazol-1-yl)-pyridine A mixture of 2,6-dibromo-4-methylpyridine (33 mmol, obtained according to the method disclosed by WO 94/22833), 3-trifluoromethyl-1H-pyrazole (21 mmol), potassium carbonate (45 mmol) and N,N-dimethylformamide ((50mL) is heated at 90 C for 4 hours. The reaction mixture is partitioned between ethyl acetate ands water. The separated organic phase is washed with brine, dried over sodium sulfate and evaporated in vacuoto provide an oily residue which is purified by flash chromatography. To yield 1.9 g of the title compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,73112-16-0, 2,6-Dibromo-4-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; EP1101764; (2001); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1018505-59-3, 5-(4-Ethylpiperazin-1-yl)pyridin-2-amine, 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, HPLC of Formula: C11H18N4, blongs to pyridine-derivatives compound. HPLC of Formula: C11H18N4

General procedure: Pd2(dba)3 (86.4mg, 0.09mmol) and Xant-phos (109.2mg, 0.19mmol) were added under N2 to a solution of 154 1E (290.0mg, 0.94mmol), INT-7 (228.6mg, 1.04mmol), and 152 potassium phosphate (400.5mg, 1.88mmol) in 111 1,4-dioxane (10mL). Then the mixture was reacted in the microwave at 150C for 1h. The mixture was cooled to RT, filtered, diluted with water (10mL), and extracted with DCM (10mL×3). The combined organic layers were washed with brine (30mL), dried over anhydrous Na2SO4, concentrated under a vacuum, and purified by preparative thin-layer chromatography to obtain 157 compound 1 (140.3mg; yield, 30%) as a yellow solid.

The synthetic route of 1018505-59-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yin, Lei; Li, Heng; Liu, Wenjian; Yao, Zhenglin; Cheng, Zhenzhen; Zhang, Huabei; Zou, Hui; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 1 – 28;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1247503-48-5 , The common heterocyclic compound, 1247503-48-5, name is 6-(2,2,2-Trifluoroethoxy)picolinic acid, molecular formula is C8H6F3NO3, 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 6-(2,2,2-trifluoroethoxy)picolinic acid (2.2 g, 10 mmol, 1.0 equiv) in methanol (20 mL) were added 2 drops of H2SO4 (con.). The mixture was stirred at 20C for 20 hours, diluted with H2O (100 mL) and extracted with DCM (3*20 mL). The combined organic phase was dried over anhydrous sodium sulfite and concentrated in vacuo. The residue was purified by silica gel chromatography (PE/EA = 20/1) to afford the title compound methyl 6-(2,2,2-trifluoroethoxy)picolinate as a colorless oil (2.1 g, 88% yield). LC-MS: m/z 236.1 (M+H)+

The synthetic route of 1247503-48-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANNAPURNA BIO, INC.; TANG, Haifeng; HANSON, Michael; BOYCE, Sarah; NIE, Zhe; (461 pag.)WO2020/73011; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem