[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[NH2:13]OS(O)(=O)=O>CN(C=O)C>[CH3:3][C:4]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[N:6]([NH2:13])[CH:5]=160% Sodium hydride (6.69 g, 167 mmol) is added to a stirred solution of 3-methyl-1H-pyrrolo[2,3-c]pyridine (1.47 g, 11.2 mmol) in DMF (33 mL) portion wise at 0° C. for 1 h. Hydroxylamine-O-sulfonic acid (6.3 g, 55.8 mmol) is added in portions at 0° C. and stirred for 2 h at 0° C. The reaction mixture is quenched at 0° C. with water, concentrated in vacuo to remove DMF. The residue is triturated in DCM. The solid is filtered off and the filtrate is concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 10% MeOH in DCM to afford 3-methyl-pyrrolo[2,3-c]pyridin-1-ylamine (1 g, 61%). MS: 148 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.85 (s, 1H), 8.27 (d, 1H), 7.46 (d, 1H), 7.09 (s, 1H), 2.30 (s, 3H).
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