4-Bromo-3-(trifluoromethyl)aniline → HCID 16050434, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-3-trifluoromethylaniline (1.77 g, 7.4 mmol), 1-methyl-5-cyano-2-pyrrole-boronic acid (2.0 g, 13.3 mmol), KF (1.42 g, 24.4 mmol), and Pd2(dba)3 (179 mg, 0.185 mmol) were added to a 50 mL round bottom flask under nitrogen. The flask was sealed and purged with nitrogen for 5 minutes. THF (18.5 mL) was added and the mixture was purged with nitrogen for an additional 5 minutes. A solution of tri-t-butylphosphine (10% wt in hexanes) (1.1 mL, 0.37 mmol) was added via syringe and the mixture was stirred vigorously at 25° C. for 16 hours. The mixture was diluted with 250 mL of EtOAc, filtered through a plug of silica gel, washed through with 200 mL of EtOAc and concentrated to give a crude brown/black semi-solid. Purification via Isco chromatography (the Redisep® column, silica, gradient 5-100% ethyl acetate in hexane) afforded 5-[4-amino-2-(trifluoromethyl)phenyl]-1-methyl-1H-pyrrole-2-carbonitrile as a white solid (1.8 g, 92%).

Provenance & Evidence