[S:1]1[C:5](B(O)O)=[CH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C1(C)C=CC=CC=1.C(O)C.[Pd]>[S:1]1[C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[CH:4]=[C:5]1[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][N:15]=1
Benzo[b]thiophene-2-ylboronic acid (997 mg, 5.6 mmol) and 1-chloroisoquinoline (946 mg, 5.8 mmol) were dissolved in toluene (20 ml) and ethanol (10 ml), and palladium catalyst (220 mg, 0.19 mmol) and 2M sodium carbonate solution (20 ml) were added thereto, followed by refluxing under a N2 atmosphere for 5 hours. The reaction solution was added to H2O, and the mixture was extracted with chloroform, followed by drying with sodium sulfate. After filtration, the filtrate was evaporated to dryness under reduced pressure. The obtained solid was purified by column chromatography (eluent: chloroform) (amount: 1.16 g, yield: 79%).
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