Potassium Carbonate → 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]acetamide

Participants

Reaction Steps

A mixture of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (260 mg, 1.00 mmol) and N,N-dimethylformiminium chloride (250 mg, 2.00 mmol) in dry 1,4-dioxane (5 mL) and DMF (1 mL) was sealed in a reaction vessel and stirred at room temperature for 10 minutes to give a white slurry. To the slurry was added 2 M aqueous potassium carbonate (2.5 mL, 5 mmol), 2-(4-bromophenoxy)acetamide (240 mg, 1.00 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (50 mg). The sealed vial was degassed with nitrogen and heated to 90° C. for 30 minutes. The reaction was quenched with water (20 mL), and extracted with EtOAc (3×20 mL). The combined organic layers were dried and concentrated in vacuo to give 2-[4-(6-chloro-3-formyl-1H-indol-5-yl)phenoxy]acetamide (250 mg, 55% yield) as a yellow solid.

Provenance & Evidence