反应详情

To a solution of 2-Amino-5-bromo-pyridine-3-carbaldehyde (632 mg, 3.14 mmol) in anhydrous THF (20 mL) was methylmagnesium bromide 3M in diethyl ether (6.06 mL, 34.8 mmol) is added at −50° C. The reaction mixture was warmed to room temperature and stirred overnight. Saturated aqueous ammonium chloride was added to the mixture (15 mL), the organic layer separated and the aqueous phase extracted with EtOAc (3×20 mL). Organic layers were dried over sodium sulfate, filtered and concentrated. The crude residue was purified by flash silica chromatography with a gradient of ethyl acetate in hexanes. (2-Amino-5-bromo-phenyl)-cyclopentyl-methanol (425.9 mg, 50% yield) was obtained as a yellow powder. MS: m/z 271/273[MH+].

1. additionis added at −50° C
2. customthe organic layer separated
3. extractionthe aqueous phase extracted with EtOAc (3×20 mL)
4. dry with materialOrganic layers were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude residue was purified by flash silica chromatography with a gradient of ethyl acetate in hexanes