Sodium Carbonate → HCID 58641236, compound

Participants

Reaction Conditions

Reaction Steps

A deoxygenated mixture of crude tert-butyl (2S)-2-phenyl-4-{[(trifluoromethyl)sulfonyl]oxy}-2,5-dihydro-1H-pyrrole-1-carboxylate (5-4, 7.65 mmol), 2,5-difluorophenyl boronic acid (1.81 g, 11.5 mmol), aqueous Na2CO3 solution (2 M, 11.5 mL, 23.0 mmol), and Pd(PPh3)4 (0.442 g, 0.383 mmol) in dioxane (100 mL) was heated at 90° C. for 45 min. The reaction mixture was cooled, then partitioned between brine (200 mL) and a 1:1 mixture of ethyl acetate and hexane (200 mL). The organic layer was dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (SiO2, 0-50% EtOAc/hexanes gradient) to provide tert-butyl (2S)-4-(2,5-fluorophenyl)-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate (5-5) as a white solid. LRMS m/z (M+H—CH3) 358.0 found, 358.2 required.

Provenance & Evidence