Potassium Phosphate, Tribasic → N-(1-(3-(3,5-difluorophenyl)-benzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,5-difluorophenylboronic acid (292 mg, 1.848 mmol), potassium phosphate (0.204 mL, 2.464 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (126 mg, 0.308 mmol), palladium (II) acetate (27.7 mg, 0.123 mmol) and N-(1-(3-bromobenzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide (444 mg, 1.232 mmol) in Toluene (10 mL) was purged with N2 for 2 min, then heated to 110° C. overnight. After 19 h, the reaction was partitioned between water and EtOAc. The organic layer was stirred over MgSO4, filtered and concentrated under reduced pressure to give amber oil. The product was purified by column chromatography on a silica gel column using 20 to 40% gradient of EtOAc in hexane as eluent to give N-(1-(3-(3,5-difluorophenyl)benzo[b]thiophen-2-yl)ethyl)-2-methylpropane-2-sulfinamide as a colorless glassy solid: 1H NMR (400 MHz, DMSO-d6) δ 1.13 (s, 9H), 1.50 (d, J=6.7 Hz, 3H), 4.64-4.73 (m, 1H), 5.91 (d, J=4.7 Hz, 1H), 7.21 (dd, J=8.4, 2.3 Hz, 2H), 7.34-7.45 (m, 4H), 8.02 (ddd, J=7.5, 1.4, 1.1 Hz, 1H); LC-MS (ESI)] m/z 394.0 [M+H]+.

Provenance & Evidence