反应详情

(5-Bromo-quinolin-2-yl)-(2-methoxy-benzyl)-amine (1000 mg, 2.92 mmol) was dissolved in 30 mL toluene. The reaction mixture was evacuated and backfilled with argon for three times to remove oxygen. Vinyltributyltin (952 mg, 3.00 mmol) and tetrakis(triphenylphosphine)palladium(0) (67 mg, 0.058 mmol) were added. The reaction mixture was refluxed overnight and evaporated. The residue was poured into 50 mL acetonitrile and extracted three times with heptane (50 mL each) to remove the tin products. The acetonitrile phase was dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient). (2-Methoxy-benzyl)-(5-vinyl-quinolin-2-yl)-amine was obtained as a light yellow gum (544 mg, 64%), MS: m/e=291.3 (M+H+).

1. customThe reaction mixture was evacuated
2. customto remove oxygen
3. temperatureThe reaction mixture was refluxed overnight
4. customevaporated
5. additionThe residue was poured into 50 mL acetonitrile
6. extractionextracted three times with heptane (50 mL each)
7. customto remove the tin products
8. dry with materialThe acetonitrile phase was dried with sodium sulfate
9. filtrationfiltered
10. customevaporated
11. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0->80:20 gradient)