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

Participants

Reaction Steps

To a suspension of 6-chloro-5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-1H-indole (210 mg, 0.80 mmol) in a solvent mixture of 1,4-dioxane/N,N-dimethylformamide=5:1 (3 mL) was added Vilsmer-salt (232 mg, 4.80 mmol) under nitrogen and the mixture was stirred at room temperature for 30 minutes. Potassium carbonate (2.0M in water, 2.0 mL) was added to the above suspension followed by the addition of 2-(4-bromophenyl)-1-(methylsulfonyl)pyrrolidine (240 mg, 0.79 mmol) in a solvent mixture of 1,4-dioxane/N,N-dimethylformamide=5:1 (3 mL) added under nitrogen. The mixture was degassed with nitrogen for 10 minutes. The mixture was treated with Pd(dppf)Cl2 (87 mg, 0.12 mmol) and stirred at 90° C. under nitrogen for 30 minutes. The mixture was filtered through a celite pad and the filtrate was partitioned between ethyl acetate (10 mL) and water (20 mL). The aqueous phase was extracted three additional times with ethyl acetate (10 mL) and the combined the organic phases were washed with brine (15 mL), dried over sodium sulfate, filtered and concentrated to afford crude which was purified by silica-gel chromatography to give the title compound (76.7 mg, 24.0% yield).

Provenance & Evidence