5-Azaindole → HCID 90094001, compound

Participants

Reaction Steps

To a solution of 1H-pyrrolo[3,2-c]pyridine (17.0 g, 0.14 mol) in 1, 2-dichloroethane (500 mL) was added AlCl3 (38.3 g, 0.29 mol) at room temperature. The mixture was stirred at room temperature for 10 minutes. A solution of 2-chloroisonicotinoyl chloride (30.0 g, 0.17 mol) in 1, 2-dichloroethane (100 mL) was added and the reaction heated to 70° C. Further AlCl3 (38.3 g, 0.29 mol) was added and the reaction was stirred at this temperature for 18 hours. The mixture was cooled to room temperature, and then to the mixture was added MeOH (150 mL) dropwise. 1M aqueous NaOH solution was added until pH=8. The mixture was filtered, the filter cake was washed with a mixture of 1/3 isopropanol/chloroform and the filtrate was extracted with a mixture of 1/3 isopropanol/chloroform (300 mL×6). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give the title compound (44 g) as a black solid, which was used in next step directly.

Provenance & Evidence