Acetate → (+/-)-[9-[(4-CHLOROPHENYL)THIO]-6-FLUORO-8-(2-METHYLPHENYL)-2,3-DIHYDRO-1H-PYRROLO[1,2-a]INDOL-1-YL]ACETIC ACID

Participants

Reaction Conditions

Reaction Steps

To (+/−)-methyl[8-bromo-9-[(4-chlorophenyl)sulfanyl]-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetate (Example 7, Step 9, 100 mg, 0.21 mmol) in 1-propanol (2 mL) were added 2-methylphenylboronic acid (57 mg, 0.42 mmol), 3:1 mixture of triphenylphosphine/palladium (>) acetate (11 mg) and 2M aqueous potassium carbonate (0.3 mL). The mixture was degassed and stirred at 80° C. for 6 h and the reaction mixture was cooled to r.t. Then THF (3 mL) and 1N LiOH were added and the mixture was stirred for 2 h at r.t. AcOH (0.5 mL) and brine were added 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 40% EtOAc/hexane containing 1% AcOH to give 90 mg of the title compound.

Provenance & Evidence