4-Fluoro-N-methoxy-N-methylbenzamide → HCID 178455444, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridine (1G) (1.0 g, 3.3 mmol) in 15 mL of ether at −75° C., is added n-butyl lithium (1.4 mL, 3.6 mmol, 2.5M in hexane) drop wise. After being stirred at −75° C. for 30 minutes, a solution of 4-fluoro-N-methoxy-N-methyl-benzamide (0.69 g, 3.8 mmol) in 5 mL of ether is added to the reaction solution drop wise. After being stirred at −75° C. for 1 hour, the reaction solution is warmed to room temperature in 1 hour, and quenched by addition of 10 mL of water. The mixture is extracted with 2×15 mL of EtOAc. After concentration, the crude product is purified by chromatography (heptane 90%, EtOAc 10%) to give [5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-3-yl]-(4-fluoro-phenyl)-methanone (1H) (0.79 g, Yield 69%) as colorless liquid. MS (ESI) m/e 346 (M+H+).

Provenance & Evidence