Sodium Carbonate → HCID 58959992, compound

Participants

Reaction Steps

A mixture of 50 mg (0.11 mmol) of 2-(3-bromobenzyl)-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol, 98 mg (0.60 mmol) of pyridine-3-boronic acid 1,3-propanediol cyclic ester, and 28 mg (0.02 mmol) of Pd[P(Ph)3]4 in 4 mL of toluene, 2 mL of EtOH, and 1 mL of 2 M aqueous sodium carbonate was warmed to reflux for 20 hours. The reaction mixture was then cooled and diluted with 5 mL of 12% aqueous ammonium hydroxide and extracted with three 5 mL portions of EtOAc. The combined organic layers were washed with three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude residue was chromatographed on silica gel using hexanes with a few drops of dichloromethane to load the sample and then eluted with EtOAc-hexanes (1:99, then 3:97, then 1:9) to afford 36 mg (72%) of a white solid. Recrystallization from ether/hexanes gave 28 mg of the title compound as a crystalline material, m.p. 148° C.-150° C.

Provenance & Evidence