Water → 6-chloro-5-{4-[2-(morpholin-4-yl)-2-oxoethyl]phenyl}-1H-indole-3-carbaldehyde

Participants

Reaction Steps

To a solution of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (153 mg, 0.581 mmol) in anhydrous 1,4-dioxane (5 mL) and DMF (1 mL) was added N,N-dimethylformiminium chloride (160 mg, 1.25 mmol). The reaction mixture was stirred at room temperature for 20 minutes, and then treated with 2N aqueous potassium carbonate (1.44 mL, 2.90 mmol) and 2-(4-bromophenyl)-1-(morpholin-4-yl)ethanone (165 mg, 0.58 mmol). The reaction was degassed with nitrogen, and treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg, 0.068 mmol). The reaction mixture was stirred at 90° C. for 30 minutes, cooled to room temperature, and poured into water (15 mL). The product was extracted with ethyl acetate (3×20 mL), and the combined organic phases were dried and concentrated in vacuo to give the title compound (249 mg, >100% yield) as a red solid, which was used in the next step without further purification.

Provenance & Evidence