Allyl bromide → HCID 68739064, compound

Participants

Reaction Steps

A solution of 5-bromo-1-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (1.05 g, 3.22 mmol) in DME (10 mL) and DMF (0.9 mL) at 0° C. was treated with NaH (116 mg, 4.8 mmol). After stirring for 20 min at RT, lithium bromide (1.67 g, 19.32 m mol) was added and the reaction mixture was allowed to stir for 1 h at RT before addition of 3-bromoprop-1-ene (0.28 ml, 3.22 mmol). The mixture was allowed to stir at 40° C. for 18 h. The mixture was quenched with brine and extracted with 2×30 mL EtOAc. The combined EtOAc layers were washed with brine, dried and concentrated. Purification on the ISCO (40 g column, 10-80% EtOAc in Hexanes) afforded 7-allyl-5-bromo-1-(2,4-difluorophenyl)-1H-pyrazolo[3,4-b]pyridin-6(7H)-one as a tan amorphous solid. MS (ESI, pos.ion) m/z: 365.9/367.9 (M+1).

Provenance & Evidence