ClCC#CCCl.C1(=O)NC(=O)C2=CC=CC=C12.[K].[Na].[N:20]1([CH2:25][C:26]#[C:27][CH2:28][N:29]2C(=O)C3=CC=CC=C3C2=O)[CH:24]=[CH:23][N:22]=[CH:21]1.NN.I.CS[C:45]1[C:53]2[CH:54]=[CH:55][CH:56]=[C:51]3[C:52]=2[C:47](=[CH:48][CH:49]=[CH:50]3)[N:46]=1.I>C(O)C>[N:20]1([CH2:25][C:26]#[C:27][CH2:28][NH:29][C:45]2[C:53]3[CH:54]=[CH:55][CH:56]=[C:51]4[C:52]=3[C:47](=[CH:48][CH:49]=[CH:50]4)[N:46]=2)[CH:24]=[CH:23][N:22]=[CH:21]1The sequential reaction of 1,4-dichloro-2-butyne with potassium phthalimide and then the sodium salt of imidazole leads to the formation of N-(4-(1H-imidazol-1yl)2-butyn-1-yl)phthalimide, which upon treatment with hydrazine in boiling ethanol leads to 4-(1H-imidazol-lyl)-2-butyn-1-ylamine. Reaction of the latter compound with 2-methylthiobenz(cd)indole hydriodide in ethanol solution, by the conditions of Example 52 leads to the hydriodide of the title compound which is converted to the free base by treatment with alkali hydroxide solution.
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