[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([CH:10]=O)[CH:9]=[C:4]2[CH:3]=[CH:2]1.Cl.[CH3:13][NH:14][CH3:15].[OH-].[Na+].C([BH3-])#N.[Na+]>CO.O>[CH3:13][N:14]([CH3:15])[CH2:10][C:8]1[CH:9]=[C:4]2[CH:3]=[CH:2][NH:1][C:5]2=[N:6][CH:7]=1
To 1H-Pyrrolo[2,3-b]pyridine-5-carbaldehyde (114 mg, 0.78 mmol), in methanol (10 ml) was added dimethylamine hydrochloride (127 mg, 1.56 mmol, NaOH (31.2 mg, 0.78 mmol), sodium cyanoborohydride (49 mg, 0.78 mmol) and the solution was stirred under nitrogen for 12 hr. Poured into water (50 mL), extracted with ethyl acetate, dried (Na2SO4) to afforded Dimethyl-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)-amine (44 mg, 33% yield) used without purification. MS: m/e 176.1 (M+H).
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