Benzyl Bromide → 1-Benzyl-4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][C:12]([CH3:14])=[CH:13][C:6]=12.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C(=O)C>[CH2:15]([N:11]1[C:7]2=[N:8][CH:9]=[CH:10][C:5]([O:4][CH3:3])=[C:6]2[CH:13]=[C:12]1[CH3:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Procedure

To a suspension of sodium hydride (0.292 g, 9.24 mmol) in dry N,N-dimethyl acetamide (10 mL) was added drop-wise under N2, a solution of 4-methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine 5 (0.60 g, 3.70 mmol) in the same solvent (5 mL). The mixture was stirred at room temperature for 45 min. After this time, the solution was cooled in an ice bath, and benzyl bromide (1.25 g, 7.30 mmol) was slowly added. The solution was allowed to warm at room temperature and stirred for 12 h. Then, it was poured into ice water (30 mL) and stirred for 30 min, and the precipitated solid was extracted with ethylacetate (3×20 mL). The organic layer was washed with water and brine. Concentration and purification on silica gel column using 20% ethylacetate in hexanes gave pure title compound 6 as a white solid. Yield: 0.70 g, 68%; mp 129-131° C.; ESI MS: m/z 253.0 (M+1).