[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10](=[N:12]O)[CH3:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCO.[ClH:23]>C1COCC1.CCOC(C)=O.CCOCC>[ClH:23].[ClH:23].[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[CH:10]([NH2:12])[CH3:11]To a heterogeneous solution of 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethanone oxime (Example 72) (0.31 g, 1.75 mmol) in THF (27.5 mL) was added lithium aluminum hydride (0.33 g, 8.79 mmol) at room temperature under a nitrogen atmosphere. The reaction mixture was refluxed for 1 h and then quenched by careful addition of hydrated Na2SO4. Ethyl acetate was added and the reaction mixture was stirred overnight. The solid was filtered off and thoroughly rinsed with EtOAc and EtOH. The filtrate was concentrated to give a yellow oil. The crude residue was dissolved in EtOAc and EtOH (100 mL; 1:1) and 2 M HCl in Et2O was added (1.85 mL). The precipitate was filtered off, rinsed with EtOAc and Et2O, and dried to provide 1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethylamine dihydrochloride (0.29 g, 72%) as a light orange solid: mp 289-292° C.; 1H NMR (300 MHz, CD3OD) δ1.82 (3H, d, J=6.9 Hz), 4.88-4.95 (1H, m), 7.09 (1H, s), 8.17 (1H, d, J=6.4 Hz), 8.29 (1H, d, J=64 Hz), 9.13 (1H, s); ESI MS m/z 162 [C9H11N3+H]+; HPLC (Method A) 97.7% (AUC), tR=6.50 min.
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