Hydrochloric Acid → HCID 59627927, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-6-fluoro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indole (D17) (980 mg, 2.366 mmol) in 1,4-dioxane (20 mL) and water (20 mL) was added potassium hydroxide (531 mg, 9.46 mmol). The reaction mixture was purged with argon and then treated with 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (60.3 mg, 0.142 mmol) and tris(dibenzylideneacetone)dipalladium(0) (43.3 mg, 0.047 mmol). The reaction mixture was heated at 90° C. for 1 hour. After cooling to room temperature, the mixture was diluted with ethyl acetate and water. The pH was adjusted to ˜7 by the addition of 1M hydrochloric acid. After separation of the layers, the aqueous phase was re-extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate, filtered and concentrated. The product was purified by silica gel chromatography eluting with 5-40% ethyl acetate in hexane to yield the title compound (D18), (382 mg).

Provenance & Evidence