Methylamine → (S)-ethyl 2-tert-butoxy-2-(7-fluoro-3-methyl-6-(methylcarbamoyl)-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A Smith process vial was charged with (S)-ethyl 2-tert-butoxy-2-(6-chloro-7-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate (131.8 mg, 0.263 mmol), 2 M methylamine in THF (0.66 mL, 1.32 mmol), molybdenum hexacarbonyl (0.069 g, 0.263 mmol), BrettPhos Palladacycle (29 mg, 0.0395 mmol), and triethylamine (0.128 mL, 0.921 mmol). Toluene (1.5 mL) was added and mixture was heated in microwave at 140° C. for 1.5 hour. The reaction mixture was diluted with ethyl acetate, washed brine, dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 50% ethyl acetate/hexanes) to give an off-white solid (19.2 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C22H26F4NO7S: 524.5; Found: 524.0.

Provenance & Evidence