Sodium hydride → HCID 68814746, compound

Participants

Reaction Steps

Dissolve methane sulfonamide (951 mg, 10 mmol) in THF (30 mL). Add sodium hydride (380 mg, 9.5 mmol, 60% dispersion in mineral oil) and reflux for 3 h, cool to room temperature and concentrate. Charge a sealed flask with sodium methansulfonamide (478 mg, 4.09 mmol), 2-chloro-6-(methylpropylamino)-isonicotinic acid methyl ester (79 mg, 3.27 mmol), biphenyl-2-yl-di-tert-butylphosphane (98 mg, 0.33 mmol), and tris(dibenzylideneacetone)dipalladium (0) (150 mg, 0.16 mmol) in toluene (7 mL). Degas with argon, seal the vessel and heat at 100° C. for 16 h. Cool to room temperature, dilute with ethyl acetate, wash with water, aqueous sodium chloride, concentrate and purify (silica gel chromatography, eluting with 0:100 to 50:50 ethyl acetate:hexanes) to give the title compound as an oil (870 mg, 88%).

Provenance & Evidence