Acetyl chloride → N-(5-Bromo-2-chloro-3-pyridinyl)acetamide

To a solution of 3-amino-5-bromo-2-chloropyridine (stage 152.1.2, 3.59 mmol) and triethylamine (1 ml) in dichloromethane (20 ml) was added acetyl chloride (Aldrich, Buchs, Switzerland, 0.312 ml). The RM was stirred for 17 h at rt then was added acetyl chloride (0.3 ml), the RM was stirred for 3 h at rt. Acetyl chloride (0.1 ml) was added and the RM was stirred for 1 h at rt. The RM was quenched with aqueous NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (heptane/EtOAc 0% to 40%). The fractions containing product were evaporated together to give the title compound as a white solid. (HPLC: tR 2.46 min (Method A); M+H=249, 251 MS-ES)

1. stirringthe RM was stirred for 3 h at rt
2. stirringthe RM was stirred for 1 h at rt
3. customThe RM was quenched with aqueous NaHCO3
4. extractionextracted with EtOAc
5. washThe organic layer was washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customevaporated
9. customThe residue was absorbed on silica gel
10. custompurified by flash chromatography (heptane/EtOAc 0% to 40%)
11. additionThe fractions containing product
12. customwere evaporated together

ORD record

ord-517afd6c7255464bb07a47b51994dd7b

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476294B2