Diethyl Ether → HCID 68739714, compound

Participants

Reaction Conditions

Reaction Steps

In a 25 mL sealed glass tube, a mixture of tetrakis(triphenylphosphine)palladium(0) (42 mg, 37 μmol), 3-borono-5-fluoro-4-methylbenzoic acid (218 mg, 1101 μmol), and 5-bromo-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (312 mg, 917 μmol) in 4.6 mL of dioxane and 1.0 M solution of sodium carbonate (2.3 mL, 2.3 mmol) was heated in a microwave at 130° C. for 30 min. The reaction mixture was treated with 15 mL of ether and washed with 5 mL of 2 N NaOH, The ether layer was discarded. The aqueous extracts were acidified to pH 4 with 5 N HCl and extracted with 3×25 mL EtOAc. The combined EtOAc layers were dried over MgSO4, filtered and concentrated in vacuo (rotovap) affording the title compound (296 mg) as a viscous oil which solidified to an off-white amorphous solid under vacuum overnight. MS (ESI, pos.ion) m/z: 414.0 (M+1).

Provenance & Evidence