Sodium Iodide → 4-Iodo-1-acetyl-7-azaindole

Participants

Reaction Steps

Compound 2 (2.7 g, 18 mmol) and NaI (13 g, 88 mmol) were dissolved in acetonitrile (28 ml). To this solution, CH3COCl (3.5 ml, 50 mmol) was added while stirring at room temperature. The reaction mixture was heated at 85° C. for 12 hours. After the reaction mixture was cooled to room temperature, 10% aqueous Na2CO3 (28 ml) and 10% aqueous NaHSO3 (28 ml) were added sequentially and stirred at room temperature for 15 minutes. The reaction mixture was washed with ethyl acetate, and the organic layer was further washed with saturated aqueous sodium chloride. After drying over anhydrous sodium sulfate, the organic layer was concentrated and purified on a silica gel column to give 4-iodo-1-N-acetyl-pyrrolo[2,3-b]pyridine (2.0 g) and 4-iodo-1H-pyrrolo[2,3-b]pyridine (Compound 3) (2.3 g). 4-Iodo-1-N-acetyl-pyrrolo[2,3-b]pyridine (2.0 g, 7.0 mmol) was dissolved in ethanol (70 ml) and, after addition of 28% sodium methoxide in methanol (1.4 ml, 7.0 mmol), was then heated under reflux for 1 hour. The reaction mixture was concentrated and then partitioned between ethyl acetate and saturated aqueous ammonium chloride, and the organic layer was washed with saturated aqueous ammonium chloride. After drying over anhydrous sodium sulfate, the organic layer was concentrated and combined with Compound 3 (2.3 g) which had been previously obtained, followed by recrystallization from ethanol to give Compound 3 (4.0 g, 92%).

Provenance & Evidence