Methyl iodide → 5-[2-Fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(methoxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide

Participants

Reaction Steps

To a suspension of NaH (9.96 mg, 0.25 mmol) in DMF (1.25 mL) at 0° C. under argon was added 5-[2-fluoro-4-(1-hydroxy-1-methylethyl)phenyl]-2-{[6-(hydroxymethyl)pyridin-2-yl]amino}thiophene-3-carboxamide (Example 43) (50 mg, 0.125 mmol) and the mixture was stirred for 20 minutes. Iodomethane (26.6 mg, 0.187 mmol) was then added and the reaction was allowed to warm to room temperature and subsequently heated to 60° C. overnight. The reaction was cooled to ambient temperature, quenched by the addition of water, extracted with ethyl acetate and concentrated in vacuo. The crude residue was reverse phase HPLC (acteonitrile/water with formic acid as a modifier) to afford the title compound.

Provenance & Evidence