Ethanol → Neopentyl glycol

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-tert-butyl 2-((4-bromo-2-methoxyphenoxy)methyl)pyrrolidine-1-carboxylate (77 mg, 0.20 mmol) in toluene (1.5 mL) was added methyl 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole-3-carboxylate (77 mg, 0.24 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (6.7 mg, 0.0080 mmol), ethanol (absolute, 0.5 mL), and potassium carbonate (2M solution in water, 0.4 mL, 0.80 mmol). Nitrogen was bubbled through the mixture for 20 min. The mixture was then sealed and heated to 90° C. After 18 h, the mixture was allowed to cool to 23° C., diluted with ethyl acetate (5 mL), and filtered through Celite. The filtrate was dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography (silica gel, 0-50% ethyl acetate in heptane) afforded the title compound contaminated with neopentyl glycol.

Provenance & Evidence