Boron trifluoride → HCID 86661596, compound

Participants

Reaction Steps

Under an argon atmosphere N-[1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-isobutyramide (0.063 g, 0.22 mmol) was mixed with N-iodosuccinimide (0.15 g, 0.65 mmol). BF3*2H2O (0.47 mL, 7.4 mmol) was added at 0° C. The dark suspension was stirred at rt for 3 h after which it was poured onto a 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (20 mL). The aqueous phase was extracted with DCM (×2) 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 EtOAc:Toluene 3:1->7:1 as the eluent to afford N-[1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-isobutyramide as a solid.

Provenance & Evidence