Methyl iodide → 3-Iodo-1-methyl-4-nitro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of sodium hydride (0.872 g, 21.80 mmol) in DMF (80 mL) was added 3-iodo-4-nitro-1H-pyrrolo[2,3-b]pyridine (D16) (4.2 g, 14.53 mmol) predissolved in DMF (20 mL) dropwise over 30 mins at 0° C. The reaction mixture was then left stirring at 0° C. for 15 mins. After which, methyl iodide (1.090 mL, 17.44 mmol) was added and the resulting reaction mixture was stirred at 0° C. for ca. 1 hour. The reaction mixture was quenched with ammonium chloride solution (ca. 150 mL). The aqueous phase was extracted with ethyl acetate (3×80 mL). The combined organic phases were dried and concentrated. Another batch of 3-iodo-4-nitro-1H-pyrrolo[2,3-b]pyridine (D16) (4.2 g, 14.53 mmol) was treated in the same way. The residue from both reactions were combined and purified by chromatography on silica, eluting with a gradient of 0-50% ethyl acetate in cyclohexane to give the title compound (6.4 g). The impure fractions were re-purified by chromatography on silica, eluting with a gradient of 0-30% ethyl acetate in cyclohexane to give another batch of the title compound (1.32 g). LCMS (A): m/z (M+H)+ 304, C8H6IN3O2 requires 303 (acidic).

Provenance & Evidence