Boron trifluoride → 1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester

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Reaction Steps

Under an argon atmosphere 1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester (4.1 g, 13.7 mmol) was mixed with N-iodosuccinimide (4.9 g, 21.9 mmol). BF3*2H2O (7.0 mL, 110 mmol) was added at 20° C. The dark suspension was stirred at rt for 24 h. NIS (2.5 g) and BF3*2H2O (2.0 mL) were added and the suspension was stirred for 24H. NIS (2.5 g) and BF3*2H2O (2.0 mL) were added and the suspension was stirred for another 24 h after which it was poured onto a 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (300 mL). The aqueous phase was extracted with DCM and the combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica using DCM-EtOAc as eluent. The title compound was obtained as a colourless solid (4.1 g).

Provenance & Evidence