[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:18][O:19][C:20]([C:22]1[S:26][C:25]2[C:27]([NH2:31])=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOC(C)=O>[CH3:18][O:19][C:20]([C:22]1[S:26][C:25]2[C:27]([NH:31][C:6]([C:5]3[CH:4]=[N:3][C:2]([Cl:1])=[CH:10][CH:9]=3)=[O:8])=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1)=[O:21]
To a solution of 6-chloronicotinic acid (1.5 eq) and triethylamine (2.0 eq) in CH2Cl2 (5 mL) was added BopCl (2.0 eq). After 15 min, 7-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (87 mg) in CH2Cl2 and 4-dimethylaminopyridine (DMAP) (1.0 eq) were added to the reaction solution above. The reaction was stirred at room temperature 12 h. The reaction was then diluted with EtOAc, and washed with NaHCO3 solution and brine. The organics were dried over MgSO4, filtered and concentrated to give a crude material which was purified by flash chromatography on silica gel (20%-50% EtOAc/hexane) to provide 100 mg (68%) of the desired 7-[(6-chloro-pyridine-3-carbonyl)-amino]-benzo[b]thiophene-2-carboxylic acid methyl ester as a light yellow solid.
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