Potassium Carbonate → 6-chloro-5-[4-(5-oxomorpholin-2-yl)phenyl]-1H-indole-3-carbaldehyde

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Reaction Steps

The mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (150 mg, 0.57 mmol) and N,N-dimethylformiminium chloride (217 mg, 1.70 mmol) in DMF/dioxane (6 mL, 1:5) was stirred at room temperature for 20 minutes. Then 2.0M potassium carbonate (3 mL), 6-(4-bromophenyl)morpholin-3-one (146 mg, 0.57 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (41 mg, 0.057 mmol) was added to the mixture. The reaction mixture was purged with nitrogen for 3 minutes, heated to 90° C. and stirred for 30 minutes. The reaction mixture was extracted with ethyl acetate (10 mL×3). The organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the title compound (150 mg, 75% yield) as a brown solid that was brought forward without further purification.

Provenance & Evidence