2-Methyl-1H-pyrrolo(2,3-c)pyridine → 2-(1-fluorocyclopropyl)-4-(5-fluoro-2-methoxyphenyl)-4-methyl-1-(1H-pyrrolo[2,3-c]pyridin-2-yl)pentan-2-ol

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Reaction Steps

To a solution of 2-methyl-1H-pyrrolo[2,3-c]pyridine (80.0 mg, 0.605 mmol) in 2 mL of THF cooled to −78° C. was added 0.70 mL of n-BuLi (1.6 M in hexanes). After 5 minutes, tert-BuOK (1 M in THF, 0.75 mL) was added and the mixture was warmed to room temperature for 1 hour. The mixture was cooled to −78° C. and the above 1-(1-fluorocyclopropyl)-3-(5-fluoro-2-methoxyphenyl)-3-methylbutan-1-one (150 mg, 0.600 mmol) was added as a solution in 0.5 mL of THF. The mixture was stirred for 30 minutes at −78° C. and warmed to room temperature. 5 mL of ethyl acetate was added and the organic phase was washed with water, dried, filtered, and evaporated. Preparative layer chromatography (developer: dichloromethane-ethanol (95:5)) gave 100 mg of the title compound as an oil that solidified on standing (45% yield).

Provenance & Evidence