Pyridine → 2-Chloro-N-(4-fluoro-2-phenylaminophenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

Chloroacetyl chloride (0.68 mL, 8.58 mmol) was added dropwise to a stirred solution of 4-fluoro-N2-phenylbenzene-1,2-diamine (1.24 g, 6.13 mmol) and pyridine (2.0 mL, 24.5 mmol) in DCM (8 mL) at 0° C. under a nitrogen atmosphere. After stirring at 0° C. for 20 min, the mixture was slowly warmed to RT and stirring at RT was continued for 2 h. The mixture was partitioned between DCM and aqueous HCl (1M, 50 mL) cooled at 0° C. and the aqueous phase was further extracted with DCM (×3). The combined organic fractions were washed with water, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 30-100% DCM in cyclohexane) to afford the title compound as a white crystalline solid (750 mg, 44%). LCMS (Method C): RT 3.42 min [M+H]+ 279.2.

Provenance & Evidence