1H-Pyrrolo(2,3-b)pyridine → HCID 18372148, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-azaindole (550 mg, 4.66 mmol), copper iodide (7.4 mg, 0.038 mmol) and potassium phosphate (1.74 g, 8.18 mmol) under a N2 atmosphere is added racemic trans-1,2-diaminocyclohexane (0.046 mL, 0.38 mmol), iodobenzene (0.436 mL, 3.9 mmol) followed by anhydrous dioxane (5 mL). The resulting suspension is heated in an oil bath at 110° C. with magnetic stirring for 24 hours. The resulting mixture is filtered through a short pad of silica gel, washing the cake well with ethyl acetate. The filtrate is evaporated to leave a brown oil. The residue is purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (4:1). Fractions containing the product are combined and the solvent evaporated, and further purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate (19:1). Clean fractions containing the product are combined and evaporated to give 758 mg of 1-phenyl-7-azaindole as a light brown oil (100% yield). 1H NMR (300 MHz, CDCl3): 8.37 (1H, dd), 7.97 (1H, dd), 7.76 (2H, d), 7.56-7.49 3H m), 7.35 (1H, t), 7.13 (1H, dd), 6.63 (1H, d).

Provenance & Evidence