Triphenylarsine → (+/-)-methyl (8-acetyl-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate

Participants

Reaction Conditions

Reaction Steps

A mixture of tris(dibenzyllideneacetone)dipalladium (281 mg, 0.3 mmol) and triphenyl arsine (367 mg, 1.2 mmol) in DMF (4 mL) was sonicated for 10 minutes and then degassed. A solution of (+/−)-methyl (8-bromo-6-fluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (Example 7, Step 8, 200 mg, 0.6 mmol) in 3 mL of DMF and 1-ethoxyvinyltri-n-butyltin (650 mg, 1.8 mmol) were added and the mixture was degassed. The reaction mixture was stirred at 90° C. for 12 hours and 1N HCl (4 mL) was added. The mixture was stirred at 90° C. for 12 hours and extracted with EtOAc. The combined organic layers were washed with 1N HCl, brine and water, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc in hexanes to provide the title compound (70% pure) as a pale yellow oil used as such.

Provenance & Evidence