[F:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]([C:16]#[N:17])=[CH:12][NH:13][C:14](=O)[C:5]=3[C:4]=2[CH:3]=1.O=P(Cl)(Cl)[Cl:20].CC(OC)(C)C>O1CCOCC1>[Cl:20][C:14]1[C:5]2[C:4]3[CH:3]=[C:2]([F:1])[CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[C:11]([C:16]#[N:17])=[CH:12][N:13]=1.[ClH:20]
To 8-fluoro-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-4-carbonitrile (23.5 g, 103 mmol) in dioxane (235 mL) was added POCl3 (95 g, 621 mmol) at 85° C. The reaction mixture was left to stir at 85° C. for 3 h, cooled to 0° C., and treated with MTBE. The reaction mixture was filtered, and washed with MTBE. The solid was treated with isopropanol, warm to 45° C. for 2 h, cooled to room temperature, filtered, washed with MTBE, and dried to afford the title compound as an HCl salt. 1H NMR (600 MHz, CD3COCD3) δ 8.68 (s, 1H); 8.15 (dd, 1H); 7.78 (dd, 1H); 7.48 (dt, 1H). LRMS (APCI) calc'd for (C12H5ClFN3) [M+H]+, 246.0. found 246.0.
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