Triphenylarsine → 1-(2,3-Dihydro-1H-isoindol-5-yl)ethan-1-one

To a stirred solution 0.72 mmol 5-iodo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (Example A38(b)) in 3 ml dioxane were added 0.05 mmol palladium(II) acetate and 0.22 mmol triphenylarsine and the mixture was stirred at RT for 10 min. 1.01 mmol 1-ethoxyvinyltributylstannane 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 resuspended in THF, 25% aqueous hydrochloric acid was added, and the mixture was stirred at RT for 3 h. The mixture was then partitioned between ethyl acetate and water and the phases were separated. The aqueous phase was made alkaline to pH 14 by addition of 30% aqueous NaOH solution and then extracted with ethyl acetate. The organic phase was then washed with brine, dried over sodium sulfate, and concentrated in vacuo to yield the title compound as a brown solid (95% yield). MS (m/e): 162.6 ([M+H]+, 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. addition25% aqueous hydrochloric acid was added
6. stirringthe mixture was stirred at RT for 3 h
7. customThe mixture was then partitioned between ethyl acetate and water
8. customthe phases were separated
9. additionby addition of 30% aqueous NaOH solution
10. extractionextracted with ethyl acetate
11. washThe organic phase was then washed with brine
12. dry with materialdried over sodium sulfate
13. concentrationconcentrated in vacuo

ORD record

ord-a667497e937643e1acf4486d81c13ac5

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188139B2