Water → 1-(benzenesulfonyl)-2-ethynyl-1H-pyrrolo[2,3-b]pyridine

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Reaction Steps

Potassium carbonate (0.97 g, 6.98 mmol) was added to a suspension of 1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-2-carbaldehyde (1.00 g, 3.49 mmol) in methanol (1.0 mL), followed by the addition of a solution of dimethyl 1-diazo-2-oxopropylphosphonate (0.81 g, 4.19 mmol) in methanol (0.2 mL). The reaction mixture was stirred at room temperature for 2 hours, after which water was added, then ethyl acetate. The layers were separated. The aqueous layer was extracted twice with ethyl acetate. The organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude was purified by flash chromatography to afford 2-ethynyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.40 g, 41%; purity 70%).

Provenance & Evidence