Category: 1206978-11-1

Synthetic Route of 1206978-11-1, Adding some certain compound to certain chemical reactions, such as: 1206978-11-1, name is 2-Bromo-3-(trifluoromethoxy)pyridine,molecular formula is C6H3BrF3NO, 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 1206978-11-1.

A microwave vial was charged with (iS,25)-l-A-(6-fluoro-l,3-beiizothiazol-2- yl)cyclopentane-l,2-di amine hydrochloride (Intermediate 1; 172 mg, 0.60 mmol), molybdenum hexacarbonyl (79 mg, 0.30 mmol), tri-tert-butylphosphonium (0587) tetrafiuoroborate (5 mg, 0.018 mmol), 2-bromo-3-(trifluoromethoxy)pyridine (145 mg, 0.60 mmol), Herrmanns Catalyst (6 mg, 6.41 muetaiotaomicron) and DBU (150 mu, 0.998 mmol) in dry 1,4-dioxane (2.4 ml). The reaction was subjected to microwave irradiation at 125 C for 25 minutes then partitioned between ethyl acetate and water. The organics were washed with water and brine, filtered through a hydrophobic frit and concentrated in vacuo. The crude material was purified by column chromatography (silica, 0 – 100% ethyl acetate / petrol then 0 – 30% methanol /’ ethyl acetate) then further purified by reverse phase preparative HPLC (eluted with acetonitriie / water containing 0.1 % ammonia) to afford the title compound. (0588) 1H NMR (400 MHz, DMSO-6) delta ppm 1.50 – 1.64 (m, 2 H), 1.68 – 1.80 (m, 2 1 1 }.. 2.07 – 2.21 (m, 2 H), 4.13 – 4.23 (m, 1 H), 4.23 – 4.33 (m, 1 H), 6.97 – 7.10 (m, 1 H), 7.26 – 7.37 (m, 1 H), 7.52 – 7.62 (m, 1 H), 7.64 – 7.74 (m, 1 H), 7.90 – 8.03 (m, 1 H), 8.14 – 8.23 (m, 1 H), 8.55 – 8.69 (m, 1 H), 8.92 – 9.02 (m, 1 H) MS ES?: 441

According to the analysis of related databases, 1206978-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; FUJIMOTO, Tatsuhiko; ROBINSON, John Stephen; WO2015/124934; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206978-11-1 ,Some common heterocyclic compound, 1206978-11-1, molecular formula is C6H3BrF3NO, 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.

3-Trifluoromethoxy picolinic acid (24); At -100 0C, butyllithium (1.56 M in hexane, 5.5 mL, 8.3 mmol, 1 eq) was added dropwise to a solution 2-bromo-3-trifluoromethoxy pyridine (23, 2.0 g, 8.3 mmol) in dried toluene (15 mL). After 2 h at -78 0C, the mixture was poured onto an excess of freshly crushed dry ice before being treated with an aqueous solution of sodium hydroxide (5%, 15 mL). The resulting aqueous layer was collected, washed with diethylether (10 mL) and acidified to pH 4 by dropwise addition of hydrochloric acid (6N, 4 mL) before being extracted with ethyl acetate (3 x 10 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford pure 3-trifluoromethoxy picolinic acid (24, 1.1 g, 5.3 mmol, 64%) as a white powder; m.p. 84-87 0C.1H NMR (CD3OD, 300 MHz): delta = 8.54 (d, J= 4.5 Hz, 1 H), 7.87 (d, J = 8.5 Hz, 1 H), 7.63 (dd, J= 8.5, 4.5 Hz, 1 H). – 19F NMR ((CD3)2CO, 282 MHz): delta = -58.7 – 13C NMR(CD3OD, 75 MHz): delta = 164.5, 147.5, 144.5, 143.4, 131.2, 127.6, 120.3 (q, J= 260 Hz).- C7H4F3NO3 (207): calcd. (%) C 40.59, H 1.95, N 6.76; found C 40.21, H 2.17, N 6.97.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206978-11-1, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206978-11-1 ,Some common heterocyclic compound, 1206978-11-1, molecular formula is C6H3BrF3NO, 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.

3-Trifluoromethoxy picolinic acid (24); At -100 0C, butyllithium (1.56 M in hexane, 5.5 mL, 8.3 mmol, 1 eq) was added dropwise to a solution 2-bromo-3-trifluoromethoxy pyridine (23, 2.0 g, 8.3 mmol) in dried toluene (15 mL). After 2 h at -78 0C, the mixture was poured onto an excess of freshly crushed dry ice before being treated with an aqueous solution of sodium hydroxide (5%, 15 mL). The resulting aqueous layer was collected, washed with diethylether (10 mL) and acidified to pH 4 by dropwise addition of hydrochloric acid (6N, 4 mL) before being extracted with ethyl acetate (3 x 10 mL). The combined organic layers were dried over sodium sulfate and evaporated to afford pure 3-trifluoromethoxy picolinic acid (24, 1.1 g, 5.3 mmol, 64%) as a white powder; m.p. 84-87 0C.1H NMR (CD3OD, 300 MHz): delta = 8.54 (d, J= 4.5 Hz, 1 H), 7.87 (d, J = 8.5 Hz, 1 H), 7.63 (dd, J= 8.5, 4.5 Hz, 1 H). – 19F NMR ((CD3)2CO, 282 MHz): delta = -58.7 – 13C NMR(CD3OD, 75 MHz): delta = 164.5, 147.5, 144.5, 143.4, 131.2, 127.6, 120.3 (q, J= 260 Hz).- C7H4F3NO3 (207): calcd. (%) C 40.59, H 1.95, N 6.76; found C 40.21, H 2.17, N 6.97.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1206978-11-1, its application will become more common.

Reference:
Patent; BAYER CROPSCIENCE AG; PAZENOK, Sergii; VORS, Jean-Pierre; LEROUX, Frederic, R.; MANTEAU, Baptiste; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE DE STRASBOURG; WO2010/40461; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1206978-11-1, Adding some certain compound to certain chemical reactions, such as: 1206978-11-1, name is 2-Bromo-3-(trifluoromethoxy)pyridine,molecular formula is C6H3BrF3NO, 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 1206978-11-1.

To a stirred mixture of 2-bromo-3- (trifluoromethoxy) pyridine (300 mg, 1.24 nMol, 1 equiv) and Zn (CN) 2 (291.2 mg, 2.48 nMol, 2 equiv) in THF (15 mL) and H 2O (3 mL) , t-BuXantPhos-Pd-G3 (197.0 mg, 0.25 nMol, 0.2 equiv) and t-BuXantPhos (171.3 mg, 0.25 nMol, 0.2 equiv) under nitrogen atmosphere at RT. The resulted mixture was stirred for 2h at 80 under nitrogen atmosphere. The solvent was removed under reduced pressure. The residue was purified by Prep-TLC (CH 2Cl 2 /MeOH 20: 1) to afford 3- (trifluoromethoxy) pyridine-2-carbonitrile (200 mg, 85.76%) as a white solid. LCMS: m/z (ESI) , [M+H] + = 188.9.

According to the analysis of related databases, 1206978-11-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DIZAL (JIANGSU) PHARMACEUTICAL CO., LTD.; QI, Changhe; TSUI, Honchung; ZENG, Qingbei; YANG, Zhenfan; ZHANG, Xiaolin; (399 pag.)WO2020/35052; (2020); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem