2-Amino-5-fluoro-N-methoxy-N-methylbenzamide → 3-Methylpyridine-2-carboxaldehyde

Participants

Reaction Steps

To a solution of 2-amino-5-fluoro-N-methoxy-N-methylbenzamide (1.0 g, 5.05 mmol) in THF (4.2 mL) was added isopropylmagnesium chloride (2.0M in THF, 5.0 mL, 10.1 mmol) at −40° C. The temperature was allowed to rise to −10° C. over 40 min then was lowered to −40° C. in an acetonitrile/dry ice bath. 3-Methyl-2-pyridinylmagnesium bromide (0.25M in THF, 20.2 mL, 5.0 mmol) was added dropwise and the solution was allowed to rise to rt over one hour. The solution was partitioned between satd ammonium chloride solution and DCM; organic extracts were concentrated then purified by silica gel column chromatography eluting with a gradient of 10-70% EtOAc in hexane to afford 2-amino-5-fluorophenyl)(3-methylpyridin-2-yl)methanone as a yellow oil: LC-MS (ESI) m/z 231.2 [M+H]+.

Provenance & Evidence