Ammonia → HCID 70921717, compound

Participants

Reaction Steps

To a suspension of 4-(3-methyl-4-nitrophenoxy)pyridin-2-amine (300 mg, 1.22 mmol) in THF (5.0 mL) and DIPEA (1.7 mL, 6.12 mmol) at 0° C. was added 2-methoxyacetyl chloride (447 μL, 4.89 mmol) in a single portion and the reaction mixture warmed to RT for 30 min. A solution of NH3 in MeOH (7M, 3.0 mL) was added and after 30 min at RT the mixture was evaporated in vacuo. The residue was partitioned between DCM (50 mL) and water (40 mL) and the organic phase was separated and dried (MgSO4) and was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 5% MeOH in DCM, isocratic elution) to afford 2-methoxy-N-(4-(3-methyl-4-nitrophenoxy)pyridin-2-yl)acetamide (210 mg, 53%) as a yellow oil; Rt 2.06 min (Method 2); m/z 318 (M+H)+ (ES+).

Provenance & Evidence