[C:1](N1C=CC=CC1=O)(N1C=CC=CC1=O)=[S:2].[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[CH:25]=[N:24][C:23]([NH2:31])=[CH:22]2.C(OCC)(=O)C>ClCCl.C(OCC)(=O)C.CCCCCC>[N:31]([C:23]1[N:24]=[CH:25][C:26]2[C:21]([CH:22]=1)=[CH:20][C:19]([O:18][CH3:17])=[C:28]([O:29][CH3:30])[CH:27]=2)=[C:1]=[S:2]To a stirring solution of 1,1′-thiocarbonyldipyridin-2(1H)-one (124.6 mg, 0.536 mmol) in dichloromethane (3 mL) was added a suspension of 6,7-dimethoxyisoquinolin-3-amine (105 mg, 0.514 mmol) in dichloromethane (5 mL). The reaction mixture was applied directly to a Biotage column in 15-25% ethyl acetate/hexane followed by 100% ethyl acetate to give 3-isothiocyanato-6,7-dimethoxyisoquinoline as a white solid. Yield 69.4 mg (55%) NMR 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 8.81 (1H, s), 7.31 (1H, s), 7.16 (1H, s), 6.98 (1H, s), 3.99 (6H, s)
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