1H-Pyrrolo(2,3-b)pyridine → HCID 66679583, 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), 3-bromo-pyridine (0.376 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 38 hours. Further copper iodide (65 mg, 0.341 mmol) is added and the resulting mixture heated in an oil bath at 110° C. for 57 hours to give a brown sludgy mixture. Filtration through a short pad of silica gel, washing the cake well with ethyl acetate and evaporation of the filtrate gives the crude product as a dark brown oil. The residue is purified by flash chromatography on a 10-gram silica gel cartridge by elution with heptane:ethyl acetate:dichloromethane (3:1:1, increasing to 32:13:5 and 24:16:10). Fractions containing the product are combined and evaporated to give 818 mg of 1-pyridin-3-yl -7-azaindole as a light brown oil (108% yield). MS: m/e 196 (M+H). 1H NMR (300 MHz, CDCl3): 9.01 (1H, br.s), 8.60 (1H, br.s), 8.39 (1H, dd), 8.30 (1H, d), 8.00 (1H, dd), 7.55 (1H, d), 7.49 (1H, dd), 7.18 (1H, dd), 6.70 (1H, d).

Provenance & Evidence