1000341-55-8

General procedure for the synthesis of 3-iodo-6-chloro-1H-pyrrolo[3,2-c]pyridine from 6-chloro-5-azaindole: To a 100 mL three-necked round-bottomed flask was added a solution of N,N-dimethylformamide (10 mL) of 6-chloro-1H-pyrrolo[3,2-c]pyridine (1.00 g, 6.55 mmol), followed by the addition of potassium hydroxide (1.40 g, 24.9 mmol). The reaction mixture was stirred at room temperature for 20 minutes, then iodine (1.66 g, 6.54 mmol, 1.00 equiv) was added to the solution. The reaction mixture was continued to be stirred at room temperature for 30 minutes. Upon completion of the reaction, the reaction mixture was diluted with distilled water (50 mL) and the precipitated solid was collected by filtration. The resulting solid was dried overnight under reduced pressure to afford the target compound 6-chloro-3-iodo-1H-pyrrolo[3,2-c]pyridine (1.70 g, 93.0% yield) as a yellow solid.Results of LCMS (ESI) analysis: retention time (RT) = 1.321 min, [M + H]+ = 279, assay method=N.

[1] Patent: WO2014/81718, 2014, A1. Location in patent: Page/Page column 135
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 2056 - 2060