Tributylvinyltin → HCID 21907008, compound

Temperature

80 °C

To a mixture of 6-bromooxindole (Procedure D, 0.50 g, 2.4 mmol), vinyltributylstannane (0.95 g, 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 16 h. 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 0.12 g (31%) of 6-vinyloxindole: 1H NMR (DMSO-d6): δ10.36 (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 16 h
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-2b30d2bc99df47caa2a6333a5be5c600

Source dataset

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06369086B1