[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:14](=O)[NH:13][CH:12]=[C:11]([C:16]#[N:17])[C:7]=3[NH:8][C:9]=2[CH:10]=1.O=P(Cl)(Cl)[Cl:20]>O1CCOCC1>[Cl:20][C:14]1[C:6]2[C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:10][C:9]=3[NH:8][C:7]=2[C:11]([C:16]#[N:17])=[CH:12][N:13]=1.[ClH:1]To a slurry of 7-chloro-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-4-carbonitrile (24.95 g, 102 mmol) in dioxane (200 mL) was added POCl3 (79 g, 512 mmol) dropwise at 93° C. The reaction mixture was left to stir at 93° C. for 5 h, cooled to room temperature, and left to stir overnight. The reaction mixture was filtered, washed with MTBE, and dried to give the title compound as an HCl salt. 1H NMR (600 MHz, CD3SOCD3) δ 13.33 (s, 1H); 8.80 (s, 1H); 8.39 (d, 1H); 7.70 (d, 1H); 7.50 (dd, 1H). LRMS (APCI) calc'd for (C12H5Cl2N3) [M+H]+, 262.0. found 261.9.
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