Acetonitrile tetrahydrofuran → 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine

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Reaction Conditions

Reaction Steps

A mixture of 5-bromo-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (8.0 g, 17.6 mmol), methoxyphenyl boronic acid (2.9 g, 19.4 mmol), dichloro[1,1′-bis(diphenyl-phosphino)ferrocene]palladium(II) dichloromethane adduct (646 mg, 0.9 mmol) in THF/Acetonitrile/saturated NaHCO3 (50 ml/50 ml/50 ml) was stirred at 50° C. overnight under nitrogen. The mixture was allowed to cool to room temperature and was extracted with ethyl acetate (3×). The combined organic layers were extracted with brine, dried with Na2SO4, decanted, and concentrated to dryness. Silica chromatography of the crude using a gradient of ethyl acetate and hexane afforded 5-bromo-3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (2.2 g, 29% yield). NMR (500 MHz, DMSO-d6) δ 0.11 (s, 9H), 1.05 (m, 2H), 3.76 (m, 2H), 3.01 (s, 3H), 5.87 (s, 2H), 7.26 (m, 1H), 7.35 (m, 1H), 7.54 (m, 1H), 7.72 (m, 1H), 8.17 (s, 1H), 8.38 (m, 1H), 8.59 (m, 1H). MS: m/z 434.1 (M+H+).

Provenance & Evidence