Acetic Anhydride → N-(5-bromo-2-methylpyridin-3-yl)acetamide

To a solution of 5-bromo-2-methylpyridin-3-amine (10.7 g, 57.5 mmol) in dichloromethane (575 mL) was added acetic anhydride (12 mL, 126.5 mmol) at 0° C. followed by triethylamine (22 mL, 158 mmol). The mixture was allowed to warm to ambient temperature and stirred for 18 hours at which point a further equivalent of acetic anhydride (6 mL, 63 mmol) was added. The mixture was stirred at ambient temperature for a further 72 hours. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate (500 mL) and the organic phase washed with saturated aqueous sodium chloride (500 mL), dried over magnesium sulfate and concentrated in vacuo to give a brown solid. This solid was triturated with 30% ethyl acetate in hexanes to yield N-(5-bromo-2-methylpyridin-3-yl)acetamide as an off-white solid, (8.28 g, 36 mmol, 63%). 1HNMR (400 MHz, CD3OD): δ ppm 8.31 (s, 1H), 8.18 (s, 1H), 2.43 (s, 3H), 2.18 (s, 3H).

1. additionwas added
2. customThe reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate (500 mL)
3. washthe organic phase washed with saturated aqueous sodium chloride (500 mL)
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customto give a brown solid
7. customThis solid was triturated with 30% ethyl acetate in hexanes

ORD record

ord-a10a8f3e732f44fe84d4fb54d227d121

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288405B2