Boron trifluoride → HCID 86661598, compound

Participants

Reaction Steps

Under an argon atmosphere Pyrrolidine-1-carboxylic acid [1-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-amide (0.085 g, 0.23 mmol) was mixed with N-iodosuccinimide (0.16 g, 0.69 mmol). BF3*2H2O (0.5 mL, 7.8 mmol) was added at 0° C. The dark suspension was stirred at rt for 4 h after which N-iodosuccinimide (0.08 g1) and BF3*2H2O (0.25 mLl) were added. The suspension was stirred for 24 h all together after which it was poured onto a 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (30 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 DCM:MeOH 97:3 as the eluent to afford Pyrrolidine-1-carboxylic acid [1-(5-iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-amide.

Provenance & Evidence