Diethyl Ether → HCID 57893459, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxaldehyde (156 mg, 0.86 mmol) in tetrahydrofuran (5 mL) was added 3.0 M phenylmagnesium bromide in diethyl ether (0.58 mL, 1.74 mmol) at −78° C. under a nitrogen atmosphere. The reaction mixture was slowly warmed to −15° C. After stirring for ca. 5 h, additional 3.0 M phenylmagnesium bromide in diethyl ether (0.15 mL, 0.45 mmol) was added. The reaction mixture was stirred for another 1 h, warming to 0° C. The reaction mixture was poured into a 2:1 solution of saturated ammonium chloride and water, and extracted with ethyl acetate (3×). The combined organic extracts were washed with water and brine, and dried over sodium sulfate. After filtration and concentration, the crude product was purified by Biotage chromatography (1 to 100% ethyl acetate in hexanes) to give (5-chloro-1H-pyrrolo[2,3-c]pyridin-2-yl)(phenyl)methanol (109 mg, 49%) as a yellow foam: 1H NMR (300 MHz, CDCl3) 8.69 (1H, s), 6.23 (1H, s), 7.33-7.61 (6H, m), 8.49 (1H, s), 8.69 (1H, br s); ESI MS m/z 259 [C14H11ClN2O+H]+.

Provenance & Evidence