[OH:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([CH:13]=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>ClCCl>[Si:15]([O:1][CH2:2][CH:3]1[CH2:12][C:11]2[C:6]3=[C:7]([CH:13]=[CH:14][N:5]3[CH2:4]1)[CH:8]=[CH:9][CH:10]=2)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]To a solution of 5-(hydroxymethyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (47 mmol) in dichloromethane (143 mL) at 0° C. was added tert-butyldimethylsilyl chloride (7.63 g, 49.4 mmol), followed by triethylamine (7.92 mL, 56.4 mmol) and dimethylaminopyridine (0.58 g, 4.7 mmol). The reaction was allowed to warm to room temperature and stirred 2 hours. The reaction was quenched with water, extracted with dichloromethane and the combined organics dried over sodium sulfate. The organic phase was concentrated under reduced pressure to provide 5-(tert-butyldimethylsilyloxy-methyl)-5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline. This material was treated essentially as described in Preparation II to provide the title compounds.
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