Methyl iodide → HCID 23036709, compound

Participants

Reaction Steps

To a suspension of 60% sodium hydride (1.76 g, 44 mmol) in dry dimethylformamide (50 mL) under nitrogen was added dropwise a solution of N-(3-fluorophenyl)-2-pyridinecarboxamide (6.87 g, 32 mmol), prepared by the process of Example 4, Step 1, in dimethylformamide (25 mL) over 30 minutes. After 30 minutes more, iodomethane (3.58 mL, 57 mmol) was added. The reaction mixture was quenched with water (500 mL), extracted with ether (3×400 mL) and further extracted with ethyl acetate (300 mL). After washing with brine the ethyl acetate layer was combined with the other organic extracts, which were dried and preadsorbed onto silica gel. Flash chromatography (250 g of silica gel gradient elution with 20-50% ethyl acetate in petroleum ether) was utilized to afford N-(3-fluorophenyl)-N-methyl-2-pyridinecarboxamide (3.81 g, 52%) m.p. 75°-78° C.

Provenance & Evidence