Sodium Carbonate → HCID 74763520, compound

Participants

Reaction Conditions

Reaction Steps

A 2-5 mL microwave vial was charged with 4-bromo-N-isobutyl-N-(2-trifluoromethyl-phenyl)-benzenesulfonamide (108 mg, 0.248 mmol), 4-(methanesulfonyl)benzene boronic acid (60 mg, 0.298 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (18 mg, 0.025 mmol), 1M Na2CO3 solution (496 μL, 0.496 mmol) and 1,4-dioxane (2.5 mL). The mixture was degassed, purged with nitrogen and heated at 150° C. for 30 minutes using microwave irradiation. The mixture was diluted with EtOAc, washed with water (2×) and brine dried over Na2SO4 and concentrated under vacuum. Purified by silica gel column chromatography (0-100% EtOAc in cyclohexane) and triturating with diethyl ether gave the title compound (99 mg, 78% yield) as a white solid. 1H NMR (400 MHz, DMSO) δ 8.06-8.03 (m, 6H), 7.85 (dd, J=7.4, 2.1 Hz, 1H), 7.80-7.74 (m, 2H), 7.69-7.60 (m, 2H), 7.07 (d, J=7.7 Hz, 1H), 3.47 (dd, J=13.4, 8.7 Hz, 1H), 3.29 (s, 3H), 3.21 (dd, J=13.4, 4.8 Hz, 1H), 1.56-1.45 (m, 1H), 0.91 (d, J=6.5 Hz, 3H), 0.74 (d, J=6.7 Hz, 3H), LCMS (m/z Method B) ES+ 512.0 [M+1]+.

Provenance & Evidence