1H-Pyrrolo[2,3-b]pyridine, 5-bromo-1-methyl-

183208-35-7

74-88-4

183208-22-2

Sodium hydride (NaH, 365 mg, 9.1 mmol) was slowly added to a solution of 5-bromo-7-azaindole (1.5 g, 7.6 mmol) in N,N-dimethylformamide (DMF, 10 mL) at 0 °C. The reaction mixture was stirred at room temperature for 1.5 hours. Subsequently, iodomethane (MeI, 1.4 g, 9.8 mmol) was added and stirring was continued overnight at room temperature. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium bicarbonate (NaHCO3) solution, followed by the addition of ammonium chloride (NH4Cl, 10 mL) solution. The mixture was separated between water (20 mL) and ethyl acetate (EA, 20 mL). The organic layer was washed sequentially with water (10 mL) and saturated brine (10 mL) and dried over anhydrous sodium sulfate (Na2SO4). The solvent was removed under reduced pressure to afford 5-bromo-1-methyl-1H-pyrrolo[2,3-b]pyridine (1.7 g, yield: quantitative) as light yellow crystals.' HNMR (300 MHz, CDCl3): δ= 8.34 (d, J = 2.1 Hz, 1H), 8.01 (d, J = 2.4 Hz, 1H), 7.18 (d, J = 3.6 Hz, 1H), 6.39 (d, J = 3.3 Hz, 1H), 3.86 (s, 3H).