Cesium fluoride → 2-(Imidazo[1,2-a]pyrazin-3-yl)furo[2,3-c]pyridin-7-amine

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Reaction Conditions

Reaction Steps

A mixture of di-tert-butyl[2-(trimethylstannanyl)furo[2,3-c]pyridin-7-yl]imidodicarbonate (0.0994 g, 0.200 mmol) in 1,4-dioxane (1.5 mL) was degassed with nitrogen for 10 min. To this mixture was added 3-bromoimidazo[1,2-a]pyrazine (0.033 g, 0.17 mmol), Pd(FPh3)4 (0.0192 g, 0.0167 mmol) and cesium fluoride (0.0850 g, 0.560 mmol). The temperature was raised to 100° C. and the mixture was heated for 16 h. Following removal of solvent, the residue was purified by ISCO chromatography (0 to 10% methanol:DCM). The resultant material was dissolved in dichloromethane (2 mL) and cooled to 0° C. To this mixture was slowly added TFA (2 mL). The ice bath was removed and the mixture was stirred for 2 h and then concentrated to a light brown residue. The residue was dissolved in DCM (30 mL) and saturated aqueous sodium bicarbonate (5 mL) was added and then the mixture was concentrated. Purification by ISCO chromatography (0 to 20% methanol:DCM) afforded 0.021 g (49%) of the title compound as an off-white solid. 1H NMR (400 MHz, CD3OD): δ=9.19 (dd, J=1.4, 4.7 Hz, 1 H), 9.17 (d, J=1.5 Hz, 1 H), 8.46 (s, 1 H), 7.76 (dd, J=4.3, 5.6 Hz, 2 H), 7.43 (s, 1 H), 7.37 (s, 1 H); MS (ESI): 252.17 [M+H]+.

Provenance & Evidence