Isobutyraldehyde → HCID 10204113, 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, 100 mg, 0.22 mmol) in THF (4 mL) at −78° C. was added 3M MeMgBr (0.26 mmol) followed by the addition of 1.3M sec-BuLi (0.31 mmol). The reaction mixture was stirred at −78° C. for 20 minutes and an excess of isobutyraldehyde was added. The reaction mixture was slowly warmed to −20° C. over a 30 minute period and quenched with saturated aqueous NH4Cl. 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 preparative HPLC using a Zorbax column eluted with 10% iPrOH in Hexanes containing 0.2% of AcOH to provide 40 mg of the title compound as a white solid.

Provenance & Evidence