Sodium Hydroxide → 4-Chloro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

The m-CBA salt of 1H-Pyrrolo[2,3-b]pyridine 7-oxide (9 g) was taken into POCl3 (46 mL, 7.5 eq.). The mixture was heated at 90° C. for 15 hours and to 106° C. for another 4 hours. The mixture was cooled to room temperature, and most of the POCl3 was distilled off under high vacuum. The residue was dissolved in CH3CN (10 mL). Water (20 mL) was added slowly to quench the reaction. The resulted mixture was adjusted to pH 9 using 10 N NaOH. The solid was filtered. The crude solid was redissolved in several ml of THF and combiflashed using 0-10% MeOH in DCM to give 4-Chloro-1H-pyrrolo[2,3-b]pyridine as a slightly yellowish solid. (4 g). MS: m/z 154.9 [MH+].

Provenance & Evidence