Month: March 2022

Adding a certain compound to certain chemical reactions, such as: 90145-48-5, 5-Bromopyridine-2-carboxamide, 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, Formula: C6H5BrN2O, blongs to pyridine-derivatives compound. Formula: C6H5BrN2O

Description 9: 5-bromopicolinonitril D9)Phosphorus oxychloride (1 1 1 g, 0.720 mol) was added to a mixture of 5- bromopicolinamide (D8) (58 g, 0.288 mol) in dry toluene (300ml) The mixture was heated to reflux for 2 hours. The mixture was poured into ice/water, and basified to pH=12 with 2N NaOH. The resulting mixture was extracted with ethyl acetate and the organic phase was washed with brine, dried over Na2S04, and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture petroleum ether/ethyl acetate 10:1 . Collected fractions, after solvent evaporation afforded the title compound (D9) (43.6 g) as a yellow solid.1 HNMR (400 MHz, CHLOROFORM-d) delta (ppm): 7.60 (d, J = 8.4 Hz, 1 H), 8.00 (dd, J = 6.0, 2.0 Hz, 1 H), 8.79 (d, J = 2.0 Hz, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,90145-48-5, 5-Bromopyridine-2-carboxamide, and friends who are interested can also refer to it.

Reference:
Patent; ROTTAPHARM S.P.A.; BORRIELLO, Manuela; ROVATI, Lucio; STASI, Luigi Piero; BUZZI, Benedetta; COLACE, Fabrizio; WO2012/76063; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 84199-61-1, 3-Acetyl-2-bromopyridine, 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, Formula: C7H6BrNO, blongs to pyridine-derivatives compound. Formula: C7H6BrNO

Synthesis of 7-phenylquinolin-5-ol (6.1) for Example 1[0271] 3-Acetyl-2-bromopyridine, 56 muL phenylacetylene, 170 muL DIPEA, 22.5 mg triphenylphosphinpalladium(II) chlorid, 3 mg Cu(I)I were suspended in 1 mL DMF under argon atmosphere and stirred for 16 h at 25 C. The mixture was diluted with DCM and extracted with diluted aq. NH3 and brine. The organic phase was concentrated and the mixture separated via flash chromatography (10 g SiO2, cyclohexane?cyclohexane/ethylacetate 70:30) to yield 40 mg 1-(2-(phenylethynyl)pyridin-3-yl)ethanone as solid. Analysis: HPLC-MS: Rt=1.21 min (method E), M+H=222

The synthetic route of 84199-61-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 1796-84-5, 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 1796-84-5 as follows.

Compound 3c (3.0 g, 13.2 mmol), 4-ethoxy-3-nitropyridine (2.7 g, 13.2 mmol) and DIPEA (1.89 g, 14.6 mmol) were dissolved in N-methylpyrrolidinone (5 ml). The reaction mixture was heated to 120 C. for 18 hours. The reaction solution was cooled, extracted with ethyl acetate, washed with water, dried over magnesium sulfate, and concentrated. Then ether was added to precipitate solids, and compound 3d (1.5 g, 33%) was obtained by suction filtration. MS: 347.2 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1796-84-5, its application will become more common.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; LIU, Hong; WU, Beili; ZHENG, Yongtang; XIE, Xin; JIANG, Hualiang; PENG, Panfeng; LUO, Ronghua; LI, Jing; LI, Jian; ZHU, Ya; CHEN, Ying; ZHANG, Haonan; YANG, Liumeng; ZHOU, Yu; CHEN, Kaixian; (94 pag.)US2017/44187; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 66909-38-4, 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.66909-38-4, name is 6-Chloro-4-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.5862, as common compound, the synthetic route is as follows.

Example 7: Preparation of [N’- (3- { [5-bromo-2- (3-chloro- pyridin-2-yl) -2ff-pyrazole- 3-carbonyl] -amino} -6-chloro- 4- methyl-pyridine-2-carbonyl) -hydrazinecarboxylic acid methyl ester (7); Step 1: Preparation of 3-amino-6-chloro-2-iodo-4- methylpyridine 5-Amino-2-chloro-4-methylpyridine (1.35 g) was dissolved in DMF (20 mL) , N-iodosuccinimide (2.59 g) was added and the reaction mixture was stirred at room temperature for 12 hours. Ethyl acetate was added and the organic layer was washed 3x with water, washed with brine, dried over MgSO4 and concentrated in vacuum. The residue was purified by column chromatography (silica 60, hexane/ethyl acetate = 3:1, Rf = 0.30) to afford 1.38 g of the title compound of as an orange solid.1H-NMR (CDCl3, TMS) delta (ppm) : 2.21 (3H, s) , 4.06 (2H, br s), 6.95 (IH, s) .

Statistics shows that 66909-38-4 is playing an increasingly important role. we look forward to future research findings about 6-Chloro-4-methylpyridin-3-amine.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; WO2008/130021; (2008); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1151989-04-6, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 1151989-04-6, name is 4-Nitrophenyl 4-(pyridin-2-yldisulfanyl)benzyl carbonate. This compound has unique chemical properties. The synthetic route is as follows.

Synthesis of compound 8.; A solution of the disulfide 4 (see Senter, P. D.; Pearce, W. E.; Greenfield, R. S. /. Org Chem. 1990, 55, 2975-2978) (7 mg, 28 mumol) in dry dichloromethane (2 mL) was added to a stirred solution of bis(4-nitrophenyl) carbonate (12.8 mg, 42 mumol) and 4-(dimethylamino) pyridine (10.3 mg, 84 mumol) in dry dichloromethane (2 mL). After being stirred at room temperature for 12 h, paclitaxel (47.8 mg, 56 mumol) was added. The reaction mixture was allowed to stir at room temperature for another 12 h (see Fardis, M.; Pyun, H.-J.; Tario, J.; Jin, H.; Kim, C. U.; Ruckman, J.; Lin, Y.; Green, L.; Hicke, B. Bioorg. Med. Chem. 2003, 11, 5051-5058; Liu, C; Schilling, J. K.; Ravindra, R.; Bane, S.; Kingston, D. G. I. Bioorg. Med. Chem. 2004, 12, 6147-6161.) Workup as described above and purification by preparative TLC (30% EtOAc/hexanes) afforded compound 8 (25.3 mg, 80%): 1H NMR (CDCl3). delta 8.48 (IH, d, / = 4.6 Hz), 8.13 (2H, d, J = 8.0 Hz), 7.71 (2H, d, / = 8.3 Hz), 7.25-7.65 (17H, m), 7.13 (IH, br dd, / = 5.1, 3.3 Hz), 6.88 (IH, d, J = 9.2 Hz), 6.29 (2H, br s), 5.97 (IH, br d, / = 9.2 Hz), 5.68 (IH, d, / = 7.0 Hz), 5.42 (IH, br s), 5.13 (IH, d, / = 12.3 Hz), 5.09 (IH, d, / = 12.3 Hz), 4.97 (IH, d, / = 9.4 Hz), 4.43 (IH, dd, J = 10.6, 6.9 Hz), 4.31 (IH, d, / = 8.5 Hz), 4.20 (IH, d, / = 8.5 Hz), 3.80 (IH, d, J = 7.0 Hz), 2.56 (IH, m), 2.44 (3H, s), 2.39 (IH, dd, J = 15.4, 9.4 Hz), 2.23 (3H, s), 2.19 (IH, dd, J = 15.4, 8.7 Hz), 1.91 (3H, s), 1.88 (IH, m), 1.68 (3H, s), 1.25 (3H, s), 1.13 (3H, s); 13C NMR (CDCl3) delta 203.8, 171.3, 169.8, 167.8, 167.1, 167.1, 159.2,154.0, 149.6, 142.6, 137.4, 136.6, 133.6, 133.4, 133.4, 132.8, 132.1, 130.2, 129.1, 129.1,129.1, 128.7, 128.7, 128.5, 127.4, 127.1, 126.5, 121.1, 119.8, 84.4, 81.1, 79.2, 77.2, 76.9, 76.4, 75.6, 75.1, 72.1, 72.1, 70.0, 58.5, 52.7, 45.6, 43.2, 35.6, 35.6, 26.8, 22.7, 22.2, 20.8, 14.8, 9.6; HRFABMS m/z 1129.3433 [M + H+] (calcd for C60H6IN2Oi6S2, 1129.3463).

According to the analysis of related databases, 1151989-04-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; VIRGINIA TECH INTELLECTUAL PROPERTIES, INC.; WO2009/62138; (2009); A1;,
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. 727356-19-6, name is 2-Bromo-6-(chloromethyl)pyridine, the common compound, a new synthetic route is introduced below. name: 2-Bromo-6-(chloromethyl)pyridine

2-Chloro-6-bromomethyl-pyridine was prepared from 2-chloro-6-methylpyridine [(638] mg, 5.0 mmol) with NBS (996.5 mg, 5.6 mmol) and AIBN (92 mg) in tetrachlorocarbon. [3-{5-] [[1- (6-CLROMO-PYRIDIN-2-YLMETHYL)-PIPERIDIN-2-YL]- [L,] 2,4] oxadiazol-3-yl}-benzonitrile (450 mg, quantitative) was obtained from [3- (5-PIPERIDIN-2-YL- [1,] 2,4] oxadiazol-3-yl) -benzonitrile (300 mg, 1.18 mmol) with crude 2-chloro-6-bromomethyl-pyridine (640 mg, 3.12 mmol) and diisopropylethylamine (762.5 mg, 5.0 mmol) in DMF (8 mL) at 80 [C] for [18] [H. IH] NMR [(CDC13),] [8] (ppm): 8.40 (d, 1H), 8.33 (dd, 1H), 7.79 (dd, 1H), 7.62 (q, 2H), 7.49 (d, [1H),] 7.18 (d, [1H),] 4.16 (t, [1H),] 3.75 (dd, 2H), 3.04 (m, [1H),] 2.49 (m, [1H),] 2.04 (m, 2H), 1.50-1. 86 (m, 4H).

The synthetic route of 727356-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14902; (2004); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 64951-08-2, 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. 64951-08-2, name is Imidazo[1,2-a]pyridine-2-carboxylic acid. A new synthetic method of this compound is introduced below.

Production Example 3 N-(Tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]imidazo[1,2-a]pyridine-2-carboxamide N-[3-(Trifluoromethoxy)benzyl]tetrahydro-2H-pyran-4-amine (242 mg), imidazo[1,2-a]pyridine-2-carboxylic acid (194 mg), EDC.HCl (199 mg), HOBt (138 mg), dimethylformamide (5 mL) and triethylamine (0.33 mL) was stirred overnight at room temperature. The solvents were distilled off under reduced pressure and following extraction with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and, thereafter, the solvents were concentrated. The residue was purified by column chromatography (NH silica gel cartridge; ethyl acetate) to give the titled compound (286 mg). 1H NMR (600 MHz, CHLOROFORM-d) d ppm 1.58-1.97 (m, 4H) 3.35-3.58 (m, 2H) 3.92-4.04 (m, 2H) 4.70-5.75 (m, 3H) 6.75-7.66 (m, 7H) 8.00-8.24 (m, 2H) (ESI pos.) m/z: 420 ([M+H]+)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,64951-08-2, Imidazo[1,2-a]pyridine-2-carboxylic acid, and friends who are interested can also refer to it.

Reference:
Patent; TAISHO PHARMACEUTICAL CO., LTD.; US2012/10414; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 885168-20-7, 2-Bromo-5-fluoro-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, Computed Properties of C6H5BrFN, blongs to pyridine-derivatives compound. Computed Properties of C6H5BrFN

5-fluoro-4-methyl-pyridine-2-carboxylic acid methyl ester18 g 2-bromo-5-fluoro-4-methyl-pyridine, 1.5 g 1, ?-bis (diphenylphosphino) ferrocene dichloropalladium (II) and 18 g sodium acetate was stirred 17 h at 80C and 5 bar carbon monoxide. The reaction was filtered and the solvent was removed. Diethylether was added to the residue and the mixture was filtered. The filtrate was evaporated to give 12 g desired product. Rt: 0.90 min. (method AB)(M+H)+: 170

The synthetic route of 885168-20-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KUELZER, Raimund; RUDOLF, Klaus; WO2013/79460; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 866807-27-4, Adding some certain compound to certain chemical reactions, such as: 866807-27-4, name is 3-Amino-6-chloropyridine-2-carboxylic acid,molecular formula is C6H5ClN2O2, 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 866807-27-4.

[0173j To a solution of 3-amino-6-chloropicolinic acid (860 mg, 4.98 mmol) in dichloromethane (50 ml) was added azetidin-3-ol hydrochloride (580 mg, 5.29 mmol), HATU (2.27 g, 5.98 mmol) and Et3N (1.5 g, 14.95 mmol). The reaction mixture was stirred at 20 C for 2 h. After 2 h, the reaction mixture was concentrated in vacuo and the crude product was purified via flash chromatography on silica gel (0-50% ethyl acetate in petroleum ether) to provide (3 -amino-6-chloropyridin-2-yl)(3 -hydroxyazetidin- 1 -yl)methanone (1.1 g, 73% yield) as a yellow solid. LCMS (ESI) [M+H] = 228.0.

According to the analysis of related databases, 866807-27-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; HEFFRON, Timothy; MALHOTRA, Sushant; WEI, BinQing; CHAN, Bryan; GAZZARD, Lewis; GANCIA, Emanuela; LAINCHBURY, Michael; MADIN, Andrew; SEWARD, Eileen; HU, Yonghan; (101 pag.)WO2018/167147; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 54916-65-3, 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. 54916-65-3, name is 5-Chloro-2-methoxynicotinic acid, molecular formula is C7H6ClNO3, 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.

5-Chloro-2-methoxy-pyridine-3 -carboxylic acid (182 mg, 0.97 mmol) and 6-[4-[(lS)- 2,2,2-trifluoro-l-methyl-ethyl]-l,2,4-triazol-3-yl]pyridin-2-amine (250 mg, 0.97 mmol) were dissolved in triethylamine (1.35 mL, 9.72 mmol). Propylphosphonic anhydride (> 50 wt % in EtOAc, 1.0 mL) was added and the reaction was heated at 80 C for 3 h. The reaction was cooled to rt, quenched by addition of MeOH (5 mL) and stirred for 1 h. The resulting solid was filtered and dried under vacuum to give the title compound (200 mg, 48 %) as a white solid. 1H NMR (400 MHz, CDCI3) d 10.37 (s, 1H), 8.58 (d, 7=2.51 Hz, 1H), 8.43 – 8.49 (m, 2H), 8.31 (d, 7=2.51 Hz, 1 H), 8.16 (dd, 7=0.75, 7.78 Hz, 1H), 7.95 (t, 7=7.91 Hz, 1H), 6.71 (quin, 7=7.22 Hz, 1H), 4.19 (s, 3H), 1.82 (d, 7=7.28 Hz, 3H). MS (ESI): 427.0 [M + H]+.

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 54916-65-3, 5-Chloro-2-methoxynicotinic acid.

Reference:
Patent; BIOGEN MA INC.; GONZALEZ LOPEZ DE TURISO, Felix; DECHANTSREITER, Michael; XIN, Zhili; JONES, John, H.; HIMMELBAUER, Martin; (0 pag.)WO2020/6031; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem