[Br:1][C:2]1[C:3]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17](O)=[O:18])[C:6]=2[CH:20]=1.C1C=CC2N(O)N=[N:32][C:30]=2C=1.CCN=C=NCCCN(C)C.CN>CN(C=O)C.CCN(CC)CC>[Br:1][C:2]1[C:3]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([NH:32][CH3:30])=[O:18])[C:6]=2[CH:20]=1A solution of 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (33 g, 77 mmol), HOBT (15.6 g, 115.5 mmol) and EDCI (22.2 g, 115.5 mmol) in DMF (250 mL) was stirred at room temperature. After 2 hours, Et3N (50 mL) and CH3NH2 (HCl salt, 17.7 g, 231 mmol) was added to the mixture, and the mixture was stirred overnight. After the solvent was removed, H2O was added and the mixture was extracted with ethyl acetate. The combined organic layer was washed with H2O, brine and concentrated in vacuo. The resulting residue was washed with EtOAc to provide the product of 5-bromo-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide (32 g, yield: 94%). 1H-NMR (DMSO-d6, 400 MHz) δ 9.55 (br s, 1H), 8.46˜8.48 (m, 1H), 8.12˜8.17 (m, 2H), 7.96 (s, 1H), 7.87 (s, 1H), 7.45˜7.50 (m, 2H), 3.16 (s, 3H), 2.93 (d, J=8.4 Hz, 3H). MS (M+H)+: 441/443.
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