Dimethylformamide → 5-Fluoro-1-methyl-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

5-Fluoro-3-iodo-1-methyl-1H-pyridin-2-one (32, 120.5 g, 476 mmol) was dissolved in 2381 mL of tetrahydrofuran and cooled to −40° C. in a dry ice acetone bath. Isopropylmagnesium chloride (310 mL, 619 mmol) was added dropwise and the mixture was stirred for 30 minutes. Then 92 mL of N,N-dimethylformamide was added and the mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched by adding 200 mL of 10% aqueous hydrochloric acid, then concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 100% ethyl acetate. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a yellow solid (33, 35 g, 226 mmol, 47.4%).

Provenance & Evidence