[NH:1]1[CH:5]=[CH:4][C:3](B(O)O)=[N:2]1.COCCOC.I[C:16]1[CH:17]=[CH:18][C:19]2[O:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[O:24]1[C:19]2[CH:18]=[CH:17][C:16]([C:3]3[CH:4]=[CH:5][NH:1][N:2]=3)=[CH:25][C:20]=2[CH2:21][CH2:22][CH2:23]1To a solution of B-(1H-pyrazol-3-yl)boronic acid (400 mg, 3.57 mmol) in a mixture of tetrahydrofuran (THF), 1,2-dimethoxyethane and water (1:2:1), was added 3,4-dihydro-6-iodo-2H-1-benzopyran (1.53 g, 5.88 mmol; prepared according to Muraki et al., Tetrahedron Lett. 1996, 37, 2441) under nitrogen atmosphere. Then potassium carbonate (980 mg, 7.14 mmol) and bis(triphenylphosphine)palladium(II) dichloride (120 mg, 0.017 mmol) were added, and the reaction mixture was heated at 90° C. for 3 h. The reaction mixture was concentrated and purified by silica gel column chromatography using 30% ethyl acetate in petroleum ether as eluant to provide the title product as solid (100 mg).
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