Acetic Anhydride → N-(1-(5-Bromo-3-fluoropyridin-2-yl)vinyl)acetamide

To a solution of 5-bromo-3-fluoro-pyridine-2-carbonitrile (10 g, 49.75 mmol) in toluene (50 ml) was added MeMgCl (24.87 ml, 74.62 mmol, 3M in THF) slowly at −10° C. The reaction mixture was stirred at −10° C. for 1 h, then acetic acid anhydride (47 ml, 497.5 mmol) was added and stirring was continued for 16 h at 25° C. The reaction was then quenched by addition of saturated aqueous NaHCO3 solution (100 ml) and the resulting mixture was stirred for another 30 minutes. The organic layer was separated, washed twice with water, with brine, dried with Na2SO4 and evaporated. The remaining residue was purified by chromatography (silica gel; hexane/EtOAc 85:15-80:20) to obtain the title compound as brown solid (8.9 g, 69%).

1. stirringstirring
2. waitwas continued for 16 h at 25° C
3. customThe reaction was then quenched by addition of saturated aqueous NaHCO3 solution (100 ml)
4. stirringthe resulting mixture was stirred for another 30 minutes
5. customThe organic layer was separated
6. washwashed twice with water, with brine
7. dry with materialdried with Na2SO4
8. customevaporated
9. customThe remaining residue was purified by chromatography (silica gel; hexane/EtOAc 85:15-80:20)

ORD record

ord-c70d889dd28e4ce998c316a3fc6fada2

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08912221B2