反应详情

温度

65 °C

A solution of 2-(4-(1-methylpiperidin-4-yl)phenyl)-4-((6-nitropyridin-3-yl)oxy)pyridine (0.199 g, 0.510 mmol) in EtOAc (10 mL) and EtOH (10 mL) was treated with tin(II) chloride dehydrate (0.575 g, 2.55 mmol), heated at 65° C. for 4 h, then heated 75° C. overnight. Additional tin(II) chloride dehydrate (300 mg) was added, the mixture heated at 80° C. for 6 h, treated with another portion of tin(II) chloride dehydrate (300 mg) and heated at 80° C. for 3 days. Additional tin(II) chloride dehydrate (300 mg) was added and the mixture heated at 80° C. overnight. The mixture was cooled to RT, concentrated to dryness, treated with EtOAc and satd. NaHCO3, filtered through diatomaceous earth and the filter cake rinsed with EtOAc/THF. The filtrate was treated with solid NaOH (2 g) and NaCl until the aqueous layer was saturated, extracted with 3:1 EtOAc/THF (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 5-((2-(4-(1-methylpiperidin-4-yl)phenyl)pyridin-4-yl)oxy)pyridin-2-amine (250 mg, >100%). MS (ESI) m/z: 361.2 (M+H+).

1. temperatureheated 75° C. overnight
2. temperaturethe mixture heated at 80° C. for 6 h
3. temperatureheated at 80° C. for 3 days
4. temperaturethe mixture heated at 80° C. overnight
5. temperatureThe mixture was cooled to RT
6. concentrationconcentrated to dryness
7. additiontreated with EtOAc and satd
8. filtrationNaHCO3, filtered through diatomaceous earth
9. washthe filter cake rinsed with EtOAc/THF
10. additionThe filtrate was treated with solid NaOH (2 g) and NaCl until the aqueous layer
11. extractionextracted with 3:1 EtOAc/THF (2×)
12. washthe combined organics were washed with brine
13. dry with materialdried over Na2SO4
14. concentrationconcentrated to dryness