Tributylvinyltin → HCID 21907008, compound

Temperature

80 °C

To a mixture of 6-bromooxindole (Procedure D, 0.50 g, 2.4 mmol), vinyltributylstannane (0.95g, 3.0 mmol), lithium chloride (0.03 g, 7.1 mmol), 2,6-di-tert-butyl-4-methylphenol (0.01 g, 0.05 mmol) in acetonitrile (25 ml) stirring at 80° C. was added dichlorobis(triphenylphosphine)palladium (II). The resulting reaction was stirred with heating for 16h. The reaction was poured into a vigorously stirring mixture of 5M potassium fluoride solution: ethyl acetate/1:1 (250 mL) and stirred for 0.75 h. The resulting biphashic mixture was filtered through a Celite 521 pad and the pad flushed with ethyl acetate (5×200 mL). The combined organic phases were washed with water (200 mL), saturated sodium chloride (200 mL) and filtered through Whatman PS 1 paper and evaporated in vacuo to a golden yellow syrup. The syrup was titurated with diethyl ether to yield several crops of tan solid. Pure samples were combined, slurried with diethyl ether, filtered, and air dried to yield 0.12g (31%) of 6-vinyloxindole: 1H NMR (DMSO-d6): δ 10.36 (s, 1H), 7.13 (d, 1H, J=7.7 Hz), 6.98 (d, 1H, J.=7.5 Hz), 6.66 (dd, 1H, J=10.9, 17.7 Hz), 5.70 (d, 1H, J=17.6 Hz), 5.18 (d, 1H, J=10.9 Hz), 3.42 (s, 2H).

1. customThe resulting reaction
2. stirringwas stirred
3. temperaturewith heating for 16h
4. additionThe reaction was poured into
5. stirringa vigorously stirring
6. filtrationThe resulting biphashic mixture was filtered through a Celite 521 pad
7. customthe pad flushed with ethyl acetate (5×200 mL)
8. washThe combined organic phases were washed with water (200 mL), saturated sodium chloride (200 mL)
9. filtrationfiltered through Whatman PS 1 paper
10. customevaporated in vacuo to a golden yellow syrup
11. customto yield several crops of tan solid
12. filtrationfiltered
13. customair dried

ORD record

ord-bbf79d46b0bc4a1e82678ea911452c02

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07129253B2