Category: 117519-09-2

Reference of 117519-09-2, 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. 117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H4ClF3N2, 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 173; 4-Bromo-2-chloro-6-trifluoromethyl-pyridin-3-ylamine; 6-Trifluoromethyl-pyridin-3-ylamine (150 g, 925 mmol) was suspended in 500 ml acetonitrile. Added to the solution was N-Chlorosuccinimide (124 g, 925 mmol) and the mixture heated at 80 C. for 2 h after which N-bromosuccinimide (165 g, 925 mmol) was added and the mixture heated at 80 C. for a further 3 h. The rm was cooled to ambient temperature, concentrated in vacuo and triturated in 100 ml diethyl ether, removing the precipitate by filtration. The resulting filtrate was concentrated in vacuo and purified by column chromatography on silica, eluting with Hept:EtOAc, 4:1 to give the title compound as a dark red oil (220 g, 86%).1H NMR (CDCl3) 4.90 (bs, 2H), 7.67(s, 1H); LRMS (ES) m/z 275/277 [MH]+

According to the analysis of related databases, 117519-09-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; US2007/197478; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, 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: C6H4ClF3N2, blongs to pyridine-derivatives compound. HPLC of Formula: C6H4ClF3N2

To a solution of 2-chloro-6-(trifluoromethyl)pyridin-3-amine (8) (5.0 g, 25 mmol) in acetonitrile (60 mL) was added NBS (5.0 g, 28 mmol). The mixture was stirred at reflux for 3 hours, concentrated and purified by silica gel chromatography and eluted with petroleum ether which gave 4-bromo-2-chloro-6-(trifluoromethyl)pyridin-3-amine (9) as a red semi-solid (6.0 g, 86% yield). 1H NMR (400 MHz, CDCl3) delta 7.68 (s, 1H), 4.93 (s, 2H). LCMS (ESI) m/z 275, 277 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; PLANKEN, Simon; CHENG, Hengmiao; COLLINS, Michael Raymond; SPANGLER, Jillian Elyse; BROOUN, Alexei; MADERNA, Andreas; PALMER, Cynthia; LINTON, Maria Angelica; NAGATA, Asako; CHEN, Ping; US2019/233440; (2019); 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.117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.Application In Synthesis of 3-Amino-2-chloro-6-(trifluoromethyl)pyridine

A solution of 3-amino-2-chloro-6-trifluoromethyl-pyridine (0.890 g), 4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-l-carboxylic acid tert-butyl ester (1.4 g) (prepared as described in WO 2006/003494) and tetrakis(triphenyl- phosphine)palladium (0.200 g) in 1 ,2-dimethoxyethane (45 ml) was treated with aqueous potassium phosphate (1.1 M) (1.92 g). The reaction mixture was stirred at 800C for 3 hours. Aqueous workup with ethyl acetate furnished a residue which was purified by chromatography on silica gel (eluent: hexane / ethyl acetate 1 :1) to give 3-amino-6- trifluoromethyl-3′,6′-dihydro-2’H-[2,4′]bipyridinyl-r-carboxylic acid tert-butyl ester (1.5 g) as a white solid. MS (ES+) 288 (M-isoprene); IH NMR (400 MHz, CDCl3) 1.50 (s, 9H), 2.61 (m, 2H), 3.67 (t, 2H), 4.10 (m, 2H), 4.21 (s, 2H), 6.11 (s, IH), 7.03 (d, IH), 7.33 (d, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; PITTERNA, Thomas; CASSAYRE, Jerome Yves; CORSI, Camilla; MAIENFISCH, Peter; WO2010/9968; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 117519-09-2, 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.117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, molecular formula is C6H4ClF3N2, molecular weight is 196.56, as common compound, the synthetic route is as follows.

A mixture of compound 2-chloro-6-(trifluoromethyl)pyridin-3-amine (5.88g, 30mmol, prepared as described in WO 20091 10475), isoamyl nitrite (7.02g, 60mmol), p-TsOH (6.19g, 36mmol), TBAB (19.32g, 60mmol) and CuBr2 (1 .40g, 6mmol) in 60ml of MeCN was stirred at room temperature for 4h. Then, the mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel to give the title compound (5.85g, 75%). 1H-NMR (300Mz, DMSO-d6): delta 7.85 (d, 1 H), 8.52 (s, 1 H); 19F-NMR (300Mz, DMSO-d6): delta -65.72 (s, 3F).

Statistics shows that 117519-09-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-2-chloro-6-(trifluoromethyl)pyridine.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; EDMUNDS, Andrew; MUEHLEBACH, Michel; STOLLER, Andre; LOISELEUR, Olivier; BUCHHOLZ, Anke; HUETER, Ottmar Franz; BIGOT, Aurelien; HALL, Roger Graham; EMERY, Daniel; JUNG, Pierre Joseph Marcel; LU, Long; WU, Yaming; CHEN, Ruifang; WO2015/715; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 117519-09-2 as follows., 117519-09-2

2-Chloro-6-(trifluoromethyl)pyridin-3-amine (3 g, 15.263 mmol, 1.000 equiv) was added into a mixture of CuBr2 (6.8 g, 30.445 mmol, 2.000 equiv) and t-BuONO (3.1 g, 30.062 mmol, 2.000 equiv) in CH3CN (100 mL). The resulting solution was stirred for 2 h at room temperature. The reaction mixture was diluted with water, extracted with diethyl ether, dried over sodium sulfate, and concentrated under vacuum. This resulted in the title compound (3 g, 75%) as a brown liquid.

The chemical industry reduces the impact on the environment during synthesis 117519-09-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; CHEN, Huifen; CHU, Yanyan; DO, Steven; ESTRADA, Anthony; HU, Baihua; KOLESNIKOV, Aleksandr; LIN, Xingyu; LYSSIKATOS, Joseph P.; SHORE, Daniel; VERMA, Vishal; WANG, Lan; WU, Guosheng; YUEN, Po-wai; WO2015/52264; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine. A new synthetic method of this compound is introduced below., 117519-09-2

A mixture of 2-chloro-6-(trifluoromethyl)pyridin-3-amine (5.0 g, 25.44 mmol), 4,4,5,5-tetramethyl-2-(prop-l-en-2-yl)-l,3,2-dioxaborolane (4.7 g, 27.98 mmol), Pd(dppf)Cl2 (1.86 g, 2.54 mmol) and K2C03 (8.79 g, 63.59 mmol) in l,4-dioxane (50 mL) and H20 (10 mL) was stirred at 80C for 7 hours under a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was concentrated. The crude residue was purified by silica gel column chromatography (0-10% EtOAc in petroleum ether) to give 3-nitro-2-(prop-l-en-2-yl)-6- (trifluoromethyl)pyridine (4.68 g, yield: 91% ) as a light yellow solid. 1H NMR (400 MHz, CDCl3) d = 7.34, (d, J= 8.4 Hz, 1H), 7.03 (d, J= 8.4 Hz, 1H), 5.54-5.53 (m, 1H), 5.36-5.34 (m, 1H), 4.22 (s, 2H), 2.18 (s, 3H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,117519-09-2, 3-Amino-2-chloro-6-(trifluoromethyl)pyridine, and friends who are interested can also refer to it.

Reference:
Patent; GENENTECH, INC.; STAFFORD, Jeffrey, A.; VEAL, James, M.; TRZOSS, Lynnie, Lin; MCBRIDE, Christopher; PASTOR, Richard, M.; STABEN, Steven, Thomas; STIVALA, Craig; VOLGRAF, Matthew; (200 pag.)WO2020/18970; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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 117519-09-2, name is 3-Amino-2-chloro-6-(trifluoromethyl)pyridine. This compound has unique chemical properties. The synthetic route is as follows. 117519-09-2

Example 117 [5-TRIFLUOROMETHYL-2- [4- (3-TRIFLUOROMETHYL-PYRIDIN-2-YL)-PIPERAZIN-1-YL]-LH-] imidazo [4,5-b] pyridine, trifluoroacetic acid salt. (a) [N2-(4-METHOXY-BENZYL)-6-TRIFLUOROMETHYL-PYNDINE-2,] 3-diamine. A mixture of the [3-AMINO-2-CHLORO-6- (TRIFLUOROMETHYL)] pyridine (416 mg, 2.1 mmol, Matrix), 4-methoxy-benzylamine (294 mg, 2.1 mmol, Aldrich) and sodium bicarbonate (265 mg, 3.2 mmol) in isoamyl alcohol (0.6 mL) was heated at [220 C] in a microwave synthesizer for 30 min. The reaction mixture was then cooled to room temperature, diluted with MeOH (5 mL), filtered and the filtrate was evaporated in vacuo. The residue was purified by preparative HPLC (gradient 0.1% trifluoroacetic acid in acetonitrile) to give the title compound as a yellow oil. MS (ESI, pos. ion) [M/Z] : 298 [(M+1)]

Statistics shows that 117519-09-2 is playing an increasingly important role. we look forward to future research findings about 3-Amino-2-chloro-6-(trifluoromethyl)pyridine.

Reference:
Patent; AMGEN INC.; WO2004/35549; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem