2-methyl-1H-pyrrolo[3,2-c]pyridine → 5-(5-fluoro-2-methoxyphenyl)-2,5-dimethyl-3-(1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)hexan-3-ol

Participants

Reaction Steps

A solution of 2-methyl-1H-pyrrolo[3,2-c]pyridine (69 mg, 0.52 mmol) in 4 mL of THF was treated with 610 μL of n-BuLi (2.5 M in hexanes) at −78° C. After 5 minutes, tert-BuOK (1 M in THF, 1.0 mL) was added and the mixture was warmed to room temperature for 1.5 hours. The orange reaction mixture was cooled to −78° C. and 5-(5-fluoro-2-methoxyphenyl)-2,5-dimethylhexan-3-one (110 mg, 0.436 mmol) in 2 mL of THF was added dropwise. The mixture was stirred at −78° C. for 30 minutes, warmed to room temperature, quenched with 10 mL of saturated ammonium chloride solution, and diluted with 20 mL of ethyl acetate. The phases were separated and the aqueous layer was extracted with two 10 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Chromatography on SiO2 (MeOH in CH2Cl2, gradient, 0% to 10%) afforded 71.4 mg (43% yield) of the product as a white solid.

Provenance & Evidence