1H-Pyrrolo(2,3-b)pyridine → HCID 58217085, compound

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Reaction Steps

2.1 5.6 g (42.0 mmol) of aluminium trichloride are added to a solution of 1.0 g (8.47 mmol) of pyrrolo[2,3-b]pyridine in 100 ml of dichloromethane, and the mixture is stirred at room temperature for 2 h. 52 ml (0.2 M, 10.09 mmol) of pent-2-ynoyl chloride dissolved in dichloromethane are then slowly added dropwise to the reaction solution. The mixture is left to stir at room temperature for a further 16 h. Saturated sodium hydrogencarbonate solution is added to the reaction mixture until neutral, and the aluminium salt precipitate is filtered off with suction. The aqueous phase is separated off and extracted twice with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The residue is employed in the next reaction without further purification. 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pent-2-yn-1-one (74% purity) is obtained as colourless oil; ESI 199.

Provenance & Evidence