Methyl trifluoroacetate → HCID 10183781, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (+/−)-[8-bromo-9-[(4-chlorophenyl)sulfanyl]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid (Example 7, 250 mg, 0.6 mmol) in THF (8 mL) at −78° C. was added 3M MeMgBr (0.7 mmol) followed by the addition of sec-BuLi (0.8 mmol, 1.3M solution). The reaction mixture was stirred at −78° C. for 5 minutes and methyl trifluoroacetate (352 mg, 2.8 mmol) was added., The reaction mixture was warmed to r.t., stirred for 4 hours and saturated aqueous NH4Cl was added. The phases were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with EtOAc/Hexanes/AcOH (20:30:1) to provide 150 mg of the title compound as a white solid.

Provenance & Evidence