Hydrogen Peroxide → (5-{2-[(Cyclopropanecarbonyl-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-6-methoxy-pyridin-3-yl)-acetic acid

Participants

Reaction Steps

To cyclopropanecarboxylic acid ethyl-[2-(2-methoxy-5-trimethylsilanylethynyl-pyridin-3-yl)-5-trifluoromethyl-benzyl]-amide (0.205 g, 0.42 mmol) in THF (2 mL) at 0° C. was added borane tetrahydrofuran complex (1M in THF; 0.48 mL, 0.48 mmol), and the reaction was stirred for 2 hours. Once no starting material was seen by analytical LCMS, MeOH (0.22 mL), hydrogen peroxide (0.04 mL, 0.43 mmol), and 3M aqueous sodium hydroxide (0.22 ml) was added, and the reaction was stirred for 1 hour. Additional hydrogen peroxide (0.1 mL) was added, and the reaction was stirred for another hour. The mixture was then acidified and extracted with EtOAc, and the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by preparative HPLC to give Compound 10.

Provenance & Evidence