反应详情

温度

70 °C

Compound K7 was obtained from 3-(6-cyclopropyl-pyridin-3-yl)-benzonitrile [prepared by the following procedure: A mixture of 3-cyanophenylboronic acid [CAS-No. 150255-96-2] (8.82 g, 60 mmol), crude 5-bromo-2-cyclopropylpyridine {prepared by the following procedure: A mixture of 2,5-dibromopyridine (11.85 g, 50 mmol), cyclopropyl zinc chloride (0.4 M in THF, 160 mL, 64 mmol), Pd(PPh3)4 (578 mg, 1 mol %) in THF (55 mL) was stirred under Argon atmosphere at 70° C. for 1.5 h. Cooled to RT, poured into sat. NaHCO3-solution, extracted with ether, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown oil (12.36 g).} (ca. 60 mmol), Pd(PPh3)4 (1.733 g, 3 mol %) and K2CO3 (13.82 g, 100 mmol) in toluene (250 mL), EtOH (22 mL) and H2O (50 mL) was stirred at 80° C. for 14 h. Cooled to RT, diluted with EtOAc, washed with sat. NaHCO3-solution and brine, dried over Na2SO4. Removal of the solvent in vacuum left a brown solid, which was purified by silica gel column chromatography with cyclohexane/-EtOAc.] (9.88 g, 44.87 mmol) by treatment with tert-butyl bromoacetate and activated zinc, followed by hydrolysis with 10% HCl according to general procedure K (method d).

1. customprepared by the following procedure
2. customprepared by the following procedure
3. temperatureCooled to RT
4. extractionextracted with ether
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. customRemoval of the solvent in vacuum
8. waitleft a brown oil (12.36 g)
9. temperatureCooled to RT
10. washwashed with sat. NaHCO3-solution and brine
11. dry with materialdried over Na2SO4
12. customRemoval of the solvent in vacuum
13. waitleft a brown solid, which
14. customwas purified by silica gel column chromatography with cyclohexane/-EtOAc
15. custom] (9.88 g, 44.87 mmol) by treatment with tert-butyl bromoacetate and activated zinc, followed by hydrolysis with 10% HCl according to general procedure K (method d)