Sodium Carbonate → 4-(2-Amino-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

A mixture of 8-bromo-6-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (1.14 g, 5 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.39 g, 7.5 mmol), dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane adduct (204 mg, 250 μmol) and an aqueous solution of Na2CO3 (2 N, 12.5 mL, 25 mmol) in dioxane (50 mL) was stirred at 110° C. over night. The reaction mixture was diluted with water and extracted twice with EtOAc. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, the solvent was evaporated under reduced pressure and the residue purified by silica gel chromatography using EtOAc as eluent. The title compound was obtained after stirring with diethyl ether, filtration and drying as a light yellow crystalline solid (1.54 g, 93%).

1. extractionextracted twice with EtOAc
2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
3. dry with materialdried over sodium sulfate
4. customthe solvent was evaporated under reduced pressure
5. customthe residue purified by silica gel chromatography

ORD 기록

ord-77f426a3870f43ada43768e0dde0d823

출처 데이터셋

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08486967B2