反应详情

温度

110 °C

A mixture of 2-bromo-5-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-4,5,6,7-tetrahydro[1,3]thiazolo[5,4-c]pyridine (300 mg, 0.75 mmol), tributyl(1-ethoxy-vinyl)tin (361 mg, 1 mmol) and Pd(PPh3)4 (92 mg, 0.08 mmol) in toluene (15 mL) is degassed with argon and heated at 110° C. in a sealed tube overnight. The mixture is cooled and saturated KF solution (10 mL) is added. The mixture is stirred at rt for 30 min, and then the layers are separated. The aqueous layer is extracted with EtOAc (15 ml) and the combined extracts are dried and evaporated. The residue is dissolved in THF (10 mL), 2N HCl (10 mL) is added and the mixture is stirred at rt for 30 min. Solid Na2CO3 is added until pH>7 and the layers are separated. The aqueous layer is extracted with EtOAc (15 ml) and the combined extracts are dried and evaporated. The residue is purified by PTLC to give the title compound as a white solid. MS (M+1): 363.0; 1H NMR (δ, CDCl3): 3.88 (s, 2H), 3.52-3.62 (m, 4H), 3.41 (s, 2H), 2.99 (s, 4H), 2.62-2.77 (m, 4H), 2.29 (q, 4H), 1.66-2.08 (m, 6H).

1. customis degassed with argon
2. temperatureThe mixture is cooled
3. additionsaturated KF solution (10 mL) is added
4. customthe layers are separated
5. extractionThe aqueous layer is extracted with EtOAc (15 ml)
6. customthe combined extracts are dried
7. customevaporated
8. dissolutionThe residue is dissolved in THF (10 mL)
9. addition2N HCl (10 mL) is added
10. stirringthe mixture is stirred at rt for 30 min
11. additionSolid Na2CO3 is added until pH>7
12. customthe layers are separated
13. extractionThe aqueous layer is extracted with EtOAc (15 ml)
14. customthe combined extracts are dried
15. customevaporated
16. customThe residue is purified by PTLC