[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][C:7]=1[O:15][CH3:16].C([BH3-])#N.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(O)(=O)C.O>[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH2:11][NH:12]2)=[CH:8][C:7]=1[O:15][CH3:16]A stirred solution of 6-(2-dimethylaminoethoxy)-5-methoxy-1H-indole (D13, 0.50 g, 2.1 mmole) in glacial acetic acid (10 ml) at room temperature was treated portionwise over 15 minutes with sodium cyanoborohydride (0.25 g, 4.0 mmole). After 2 hours the solution was diluted with water (50 ml), basified by addition of Na2CO3 and then extracted with ethyl acetate (2×50 ml). The combined extract was dried (Na2 SO4), and concentrated in vacuo to leave the title compound as a brown oil (0.37 g, 73%).
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