Triphenylarsine → 5-Trifluoromethyl-6-vinyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester

To a stirred solution 0.61 mmol 5-iodo-6-trifluoromethyl-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (Example A35(d)) in 3 ml dioxane were added 0.04 mmol palladium(II) acetate and 0.18 mmol triphenylarsine and the mixture was stirred at RT for 10 min. 0.91 mmol vinyltributylstannane was then added and the mixture was heated at 100° C. for 16 h. The reaction mixture was then cooled to room temperature, filtered, and the filtrate was concentrated in vacuo. The residue was purified by chromatography (SiO2, heptane/ethyl acetate) to yield the title compound as a yellow solid (93% yield). MS (m/e): 258.0 ([M+H-Me2C═CH2]+, 100%).

1. temperaturethe mixture was heated at 100° C. for 16 h
2. temperatureThe reaction mixture was then cooled to room temperature
3. filtrationfiltered
4. concentrationthe filtrate was concentrated in vacuo
5. customThe residue was purified by chromatography (SiO2, heptane/ethyl acetate)

ORD record

ord-efc747ba3b824a979f39c74d2f953d2a

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188139B2