反应详情

温度

80 °C

N-(3-Bromo-4-chlorophenyl)-3-furamide (Intermediate 1, 63 mg), N-cyclopropylmethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzamide (60 mg), tetrakis(triphenylphosphine) palladium (5 mg) and aqueous sodium carbonate (2N, 0.5 ml) were mixed in DMF (1.2 ml) and heated at 80° C. under nitrogen for 18 hrs. The cooled reaction was absorbed onto silica, applied to an SPE (Si) and eluted with an ethyl acetate/cyclohexane gradient (0-100% ethyl acetate). The product fractions were reduced to dryness under vacuum and triturated with ether to give N-(6-chloro-4′-{[(cyclopropylmethyl)amino]carbonyl}-1,1′-biphenyl-3-yl)-3-furamide. NMR; δH [2H6]—DMSO 10.10,(1H, s), 8.65,(1H, t), 8.38,(1H, s), 7.94,(2H, d), 7.80,(3H, m), 7.54,(3H, m), 6.98,(1H, s), 3.16,(2H, t), 1.06,(1H, m), 0.43,(2H, m), 0.24,(2H, m). LCMS MH+395/397, retention time 3.32 minutes.

1. customThe cooled reaction
2. customwas absorbed onto silica
3. washeluted with an ethyl acetate/cyclohexane gradient (0-100% ethyl acetate)
4. customtriturated with ether