反应详情

温度

0 °C

To 7-chlorothienopyridine (0.95 g, 5.6 mmol) in THF (75 mL) at −78° C. was added n-butyllithium (2.5 M in hexanes, 2.4 mL, 6.0 mmol), dropwise. The solution was stirred for 30 min then warmed to 0° C. and zinc chloride (1.0 M in ether, 6.5 mL, 6.5 mmol) was added. The reaction mixture was stirred for 20 min, then bromide 291 (1.25 g, 4.64 mmol) and tetrakis(triphenylphosphine) palladium (0.5.4 g, 0.46 mmol) in THF (15 mL) were added. The mixture then was heated to reflux for 3 h and cooled to RT. The excess base was quenched with 1 mL saturated aqueous ammonium chloride, and the mixture was concentrated. The residue was partitioned between water and diethyl ether, producing a yellow precipitate, which was isolated by suction filtration, triturated with ethyl acetate and dried in vacuo to give title compound 292 (1.2 g, 72%). MS (M+H): 358.3

1. stirringThe reaction mixture was stirred for 20 min
2. temperatureThe mixture then was heated
3. temperatureto reflux for 3 h
4. temperaturecooled to RT
5. customThe excess base was quenched with 1 mL saturated aqueous ammonium chloride
6. concentrationthe mixture was concentrated
7. customThe residue was partitioned between water and diethyl ether
8. customproducing a yellow precipitate
9. customwhich was isolated by suction filtration
10. customtriturated with ethyl acetate
11. customdried in vacuo