Water → 7-Ethenyl-1H-indole

Temperature

100 °C

To 7-bromo-1H-indole (6.0 g, 30.6 mmol) in 150 mL of dimethylformamide was added tributyl(vinyl)tin (9.8 mL, 33.7 mmol), triphenylphosphine (0.4 g, 1.53 mmol), diphenyl-palladium(II) dichloride (1.07 g, 1.53 mmol) and lithium chloride (4.0 g, 94.4 mmol), and the resulting mixture was heated at 100° C. overnight. The reaction mixture was cooled to 20-24° C. and poured into 150 mL of water and 150 mL of ethyl acetate. The aqueous layer was washed with additional ethyl acetate (3×100 mL) and the combined organic layers were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 5-10% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 3.5 g (80%) of the desired compound as a clear oil.

1. temperatureThe reaction mixture was cooled to 20-24° C.
2. washThe aqueous layer was washed with additional ethyl acetate (3×100 mL)
3. washthe combined organic layers were washed with saturated aqueous sodium chloride
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. washeluting with 5-10% ethyl acetate in hexanes
8. additionFractions containing product
9. concentrationconcentrated under reduced pressure

ORD record

ord-0cfbd83475514974a0e7c40b96b6fc3f

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06743785B2