Sodium Methoxide → {(S)-1-[6-Fluoro-1-(6-methoxypyridin-3-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A suspension of {(S)-1-[4-fluoro-2-(6-fluoropyridin-3-ylamino)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester (196 mg, 0.50 mmol) in 0.5M NaOMe in MeOH (2.0 mL, 1.0 mmol) was heated at 120° C. using microwave irradiation for 15 min. The crude reaction mixture was diluted with MeOH and loaded onto an Isolute®SCX-2 cartridge then washed with MeOH followed by 2M NH3/MeOH. The basic fractions were combined and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-5% MeOH in DCM) to afford the title compound as a pink oil (52 mg, 27%). LCMS (Method C): RT 3.42 min [M+H]+ 387.2.

Provenance & Evidence