[S:1]1[CH:5]=[C:4](B(O)O)[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].O.O=[CH:23][C:24]([OH:26])=[O:25]>C(#N)C>[S:1]1[CH:5]=[C:4]([CH:23]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([F:13])[CH:15]=2)[C:24]([OH:26])=[O:25])[C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2A mixture of benzo[b]thiophen-3-ylboronic acid (400 mg, 2.25 mmol), 3-fluoroaniline (217 μl, 2.25 mmol), and 2-oxoacetic acid hydrate (207 mg, 2.25 mmol) in acetonitrile (20 ml) was stirred at room temperature for 4 hours. The solvent was removed under vacuum and the crude was used as such in the next step.
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