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レコード

ord-a0282742bda140619173d81aab7da880

出典データセット

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08901305B2