Acetyl chloride → N-(5-bromo-4-chloropyridin-2-yl)acetamide

To a stirred solution of 5-bromo-4-chloropyridin-2-amine (11.6 g, 55.9 mmol) in pyridine (100 mL) at 0° C. was added acetyl chloride (3.98 mL, 55.9 mmol) and the reaction was stirred at rt for 3 h. The reaction mixture was quenched with cold water and concentrated under reduced pressure. The residue was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with water (100 mL), brine (100 mL) and dried over sodium sulfate. The organics were concentrated under reduced pressure to afford N-(5-bromo-4-chloropyridin-2-yl)acetamide (14.6 g, 55.9 mmol, 100% yield) as a white solid that was carried on without further purification. LC/MS (ESI) m/e 249 [(M+H)+, calcd for C7H7BrClN2O 248.9], LC/MS retention time (method B): tR=1.64 min; 1H NMR (400 MHz, DMSO-d6) δ 10.87 (s, 1H), 8.58 (s, 1H), 8.33 (s, 1H), 2.11 (s, 3H).

1. customThe reaction mixture was quenched with cold water
2. concentrationconcentrated under reduced pressure
3. additionThe residue was diluted with water (50 mL)
4. extractionextracted with EtOAc (3×50 mL)
5. washThe combined organic layers were washed with water (100 mL), brine (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationThe organics were concentrated under reduced pressure

ORD record

ord-a0282742bda140619173d81aab7da880

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08901305B2