Sodium Carbonate → N-{3-[2-(2,4-Dichloro-benzoyl)-3-methoxy-benzofuran-6-yl]-benzyl}-methanesulfonamide

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Reaction Steps

(6-Bromo-3-methoxybenzofuran2-yl)(2,4-dichloro-phenyl)methanone (110 mg, 0.264 mmol), prepared as described above was dissolved in toluene/ethanol (1:1 8 mL). To this solution was added N-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-methanesulfonamide (99 mg, 0.317 mmol) and aqueous sodium carbonate (2M, 1.59 mmol). The mixture was degassed with nitrogen for 30 minutes and then Pd(dppf)2Cl2 (19.32 mg, 0.03 mmol) was added. The resultant mixture was heated at 85 deg C for 18 hours at which time it was cooled to ambient and concentrated via rotary evaporation. The oil thus obtained was diluted with EtOAc and washed with water and brine and dried over MgSO4. The organic layer was filtered and concentrated and purified by HPLC to give the desired compound (40.4 mg, 29%) 1H-NMR (CDCl3): δ 7.84 (d, 1H), 7.63-7.25 (m, 9H), 4.85 (br t, 1H), 4.40 (d, 2H), 4.24 (s, 3H), 2.95 (s, 3H), (M+H) 506.1 RT=3.66 min.

Provenance & Evidence