[NH2:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[C:5]([C:6]#[N:7])=[CH:4][N:3]=1.[H-].[Na+].[CH2:22]([NH:25][C:26](=O)[O:27]C1C=CC=CC=1)CC.[Cl-].[NH4+]>CN(C)C=O>[CH3:22][NH:25][C:26]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][C:8]3[C:5]([C:6]#[N:7])=[CH:4][N:3]=[C:2]([NH2:1])[CH:9]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)=[O:27]
6-Amino-4-(1H-5-indolyloxy)nicotinonitrile (63 mg, 0.252 mmol) was dissolved in N,N-dimethylformamide (1 ml); and sodium hydride (60% in oil, 11.6 mg, 0.29 mmol) was gradually added thereto while stirring at room temperature. After the reaction mixture was stirred for 30 minutes, phenyl N-propylcarbamate (49.5 mg, 0.277 mmol) was added thereto; and the reaction mixture was stirred for 3 hours. A saturated aqueous solution of ammonium chloride was added thereto; this was subjected to extraction with ethyl acetate, and dried over anhydrous sodium sulfate. This solution was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate-methanol) to yield the title compound (12 mg) and N1-methyl-5-(2-amino-5-cyano-4-pyridyl)oxy-1H-1-indolecarboxamide (17 mg).
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