[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:11]1[C:20]2[CH:21]=[CH:22][S:23][C:19]=2[C:18]2[CH:17]=[CH:16][C:15]([C:24]#[N:25])=[CH:14][C:13]=2[N:12]=1.O>CN(C=O)C>[O:7]([C:11]1[C:20]2[CH:21]=[CH:22][S:23][C:19]=2[C:18]2[CH:17]=[CH:16][C:15]([C:24]#[N:25])=[CH:14][C:13]=2[N:12]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Phenol (2.0 eq, 85 mg) was dissolved in anhydrous DMF. 60% sodium hydride (2.0 eq, 36 mg) was added and the reaction mixture stirred for a few minutes. 4-chlorothieno[3,2-c]quinoline-7-carbonitrile (1.0 eq, 110 mg) was added to the mixture and the whole reaction was stirred at 100° C. for two days. Water was added and the solid was filtered and dried. 4-phenoxythieno[3,2-c]quinoline-7-carbonitrile was isolated as a solid (114 mg). LCMS (ES)>95% pure, m/z 303 [M+1]+.
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