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

Temperature

90 °C

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.

1. customwas sonicated for 10 minutes
2. customdegassed
3. customthe mixture was degassed
4. addition1N HCl (4 mL) was added
5. stirringThe mixture was stirred at 90° C. for 12 hours
6. extractionextracted with EtOAc
7. washThe combined organic layers were washed with 1N HCl, brine and water
8. dry with materialdried over Na2SO4
9. concentrationconcentrated
10. customThe residue was purified by silica gel chromatography
11. washeluted with 20% EtOAc in hexanes

ORD record

ord-8428b7c4eb874f2fa24d223c79334b9a

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07144913B2