Dimethylformamide → HCID 68553177, compound
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.CC([O-])(C)C.[K+].O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.C[N:33](C=O)C>>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][N:7]=[CH:8][CH:9]=2)[N:4]([NH2:33])[CH:3]=1Participants
5
Procedure
A mixture of 3-methyl-1H-pyrrolo[2,3-c]pyridine (1.21 g, 9.16 mmol), KOtBu (2.05 g, 18.3 mmol) in DMF (41 mL) is purged with N2 and stirred at rt for 2 h. Chloramine in ether (0.15 M, 92 mL) is added and the mixture is stirred for 20 min. The reaction is cooled to 00 C. and a solution of Na2S2O3 (5 g) in water (80 mL) is added. The mixture is stirred for 10 min, and then concentrated in vacuo. The residue is triturated in DCM and filtered. DCM is added, cooled to 0° C. and charged with BOC2O (541 mg, 2.48 mmol). The resulting mixture is separated by silica gel chromatography eluting with 10% MeOH in DCM to afford 3-methyl-pyrrolo[2,3-c]pyridin-1-yl amine (468 mg, 35%). 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).