Dichloromethane → 1-(Phenylacetyl)-5-(4-pyridinyl)indoline

Temperatur

100 °C

To a solution of 5-bromo-1-(phenylacetyl)indoline (15.98 g) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (12.4 g) in 1,2-dimethoxyethane (500 mL) were added [1,1′-bis-(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1.24 g) and potassium phosphate (32.2 g) at ambient temperature and the mixture was stirred at 100° C. for 60 hours. The mixture was evaporated in vacuo to remove 1,2-dimethoxyethane and the residue was dissolved in a mixture of ethyl acetate (600 mL) and water (300 mL). The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to give 1-(phenylacetyl)-5-(4-pyridinyl)indoline (8.02 g) as a white powder.

1. customThe mixture was evaporated in vacuo
2. customto remove 1,2-dimethoxyethane
3. dissolutionthe residue was dissolved in a mixture of ethyl acetate (600 mL) and water (300 mL)
4. washThe separated organic layer was washed with brine
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate

ORD-Eintrag

ord-ddba1c18feda415aba0fbfac60cffdf3

Quelldatensatz

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08211919B2