Sodium Carbonate → HCID 58902477, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-5-(trifluoromethyl)aniline (1.50 mL, 10.6 mmol), water (15.0 mL), 1,2 dimethoxyethane (75 mL), [1-(tert-butoxycarbonyl)-1H-pyrrol-2-yl]boronic acid (3.36 g, 15.9 mmol) and sodium carbonate (4.50 g, 42.4 mmol) was degassed with nitrogen for 5 min. Tetrakis(triphenylphosphine)palladium(0) (0.74 mg, 0.64 mmol) was added to the mixture and the slurry was heated at 80° C. for 3 h. Water was added and the mixture was extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on basic alumina to give tert-butyl 2-[3-amino-5-(trifluoromethyl)phenyl]-1H-pyrrole-1-carboxylate (2.58 g, 74%). LCMS: (FA) ES+ 327.3.

Provenance & Evidence