Phosgene → HCID 57786672, compound

Participants

Reaction Steps

To a cooled solution of 2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (233 mg, 1.00 mmol) in 6 mL of dichloromethane were added 0.52 mL (3.00 mmol) of diisopropylethylamine and 0.55 mL of a 20% solution of phosgene in toluene at 0 C. The reaction mixture was stirred at 0 C for 10 minutes and pyrrolidine was added. The reaction mixture was stirred at 0 C for 1 hour then applied to column chromatography without workup. Chromatography (20->50% in hexanes/ethyl acetate in 20 minutes->100% in 30 minutes) gave 195 mg (0.591 mmol, 59%) of the title compound.

Provenance & Evidence