Tributylvinyltin → HCID 59006385, compound

3-Bromo-2-nitropyridine (1.015 g, 5.0 mmol), tetrabutylammonium chloride (1.390 g, 5.00 mmol), and bis(triphenylphosphine)palladium(II) chloride (0.351 g, 0.500 mmol) were combined. Mixture was suspended in acetonitrile (10 ml). The mixture was stirred at room temperature for 30 minutes while it was degassed by a flow of nitrogen. Tributyl(vinyl)tin (1.754 ml, 6.00 mmol) was added and the mixture was further degassed for 5 minutes. The vial was capped and heated at 90° C. for 4 hours. Solvents were removed from the mixture. The residue was dissolved with dichloromethane. Material was washed with brine and the aqueous phase was discarded. Organic layer was dried over Na2SO4, and filtered. Solvents were removed by roto-vap. Silica gel chromatography afforded the title compound as tan solid in 68% yield. 1H NMR (500 MHz, CHLOROFORM-D) δ ppm 8.39 (dd, J=4.58, 1.53 Hz, 1 H) 8.06 (dd, J=7.94, 1.53 Hz, 1 H) 7.55 (dd, J=7.93, 4.58 Hz, 1 H) 6.90 (dd, J=17.24, 11.14 Hz, 1 H) 5.82 (d, J=17.40 Hz, 1 H) 5.55 (d, J=10.99 Hz, 1 H).

1. customwas degassed by a flow of nitrogen
2. customthe mixture was further degassed for 5 minutes
3. customThe vial was capped
4. temperatureheated at 90° C. for 4 hours
5. customSolvents were removed from the mixture
6. dissolutionThe residue was dissolved with dichloromethane
7. washMaterial was washed with brine
8. dry with materialOrganic layer was dried over Na2SO4
9. filtrationfiltered
10. customSolvents were removed by roto-vap

ORD record

ord-080643b20ac1432d94f142df186b4e2e

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470680B2