[I:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=O)[C:5]=3[CH:12]=[CH:13][CH:14]=2.Cl.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C[Si](C)(C)N[Si](C)(C)C>[CH2:16]([N:23]=[C:6]1[C:5]2[CH:12]=[CH:13][CH:14]=[C:3]3[C:4]=2[C:8](=[CH:9][CH:10]=[C:2]3[I:1])[NH:7]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1The product of the example was also prepared using the procedures of Method B as described in Example 21. 6-Iodo-1H-benzo[cd]indol-2-one (0.2 g, 0.68 mmol), benzylamine hydrochloride (0.195 g, 1.36 mmol) and p-toluenesulfonic acid monohydrate (0.01 g, 0.052 mmol) were stirred in hexamethyldisilazane (0.45 ml) for 3 h at 130°. Workup as before provided the crude product. Crystallization from EtOAc-ether gave 0.172 g (66%) of a dark yellow solid: mp 160-163°; NMR (CDCl3) δ 4.90 (s, 2H), 6.99 (d, J=7.3, 1H), 7.36 (m, 3H), 7.46 (m, 2H), 7.62 (m, 1H), 7.78 (m, 1H), 7.87 (m, 2H). MS (EI) m/z 385 (M+H calcd. for C18H14IN2 385).
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