Реакция #1698688

Уравнение реакции

3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]aniline

pyridine hydrochloride

4-chlorothieno[2,3-b]pyridine-5-carbonitrile

→

4-[(3-chloro-4-[(1-methyl-1H-imidazol-2-yl)thio]phenyl)amino]thieno[2,3-b]pyridine-5-carbonitrile

Выход 26.6%

Растворители

2-ethoxyethanol

Условия реакции

Обработка

1. 1
   Температураis heated
2. 2
   Температураat reflux for 24 hours
3. 3
   ТемператураThe solution is cooled
4. 4
   Другоеthe solvent is evaporated
5. 5
   workup.ADDITIONThe resultant residue is treated with a minimum amount of methanol
6. 6
   Другоеthe product is purified by flash column chromatography
7. 7
   Промывкаeluting with 3% methanol in dichloromethane
8. 8
   workup.ADDITIONThe fractions containing product
9. 9
   Концентрированиеconcentrated
10. 10
    workup.ADDITIONEthyl acetate is added
11. 11
    Фильтрацияthe insoluble material collected by filtration

Методика

A mixture of (3-chloro-4-[(1-methyl-1H-imidazol-2-yl)sulfanyl]aniline (135 mg, 0.57 mmol), pyridine hydrochloride (66 mg, 0.57 mmol) and 4-chlorothieno[2,3-b]pyridine-5-carbonitrile (0.1 g, 0.52 mmol) in 4 mL of 2-ethoxyethanol is heated at reflux for 24 hours. The solution is cooled and the solvent is evaporated. The resultant residue is treated with a minimum amount of methanol and the product is purified by flash column chromatography eluting with 3% methanol in dichloromethane. The fractions containing product are combined and concentrated. Ethyl acetate is added and the insoluble material collected by filtration to provide 55 mg of 4-[(3-chloro-4-[(1-methyl-1H-imidazol-2-yl)thio]phenyl)amino]thieno[2,3-b]pyridine-5-carbonitrile as a tan solid, mp>240° C.; 1H NMR (DMSO-d6) δ 3.61 (s, 3H), 6.53 (d, J=9 Hz, 1H), 7.15 (m, 1H), 7.17 (s, 1H), 7.44 (m, 1H), 7.52 (s, 1H), 7.54 (s, 1H), 7.81 (d, J=6 Hz, 1H), 8.53 (s, 1H), 9.76 (s, 1H); MS 396.2 (M−H)−.

Источник