Реакция #7587

Уравнение реакции

potassium carbonate

2-chloromethyl-1-methylimidazole

4-chloro-7-hydroxy-6-methoxycinnoline

→

4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline

Выход 29.0%

Растворители

DMF

water

Условия реакции

Обработка

1. 1
   Другое(prepared
2. 2
   ЭкстракцияAfter extraction with ethyl acetate the organic layer
3. 3
   Промывкаwas washed with water
4. 4
   Сушкаbrine, dried (MgSO4)
5. 5
   Другоеthe solvent evaporated
6. 6
   ДругоеThe residue was purified by flash chromatography

Методика

The starting material, 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]-cinnoline was obtained by adding potassium carbonate (531 mg, 3.8 mmol) followed by 2-chloromethyl-1-methylimidazole (232 mg, 1.4 mmol) to a suspension of 4-chloro-7-hydroxy-6-methoxycinnoline (270 mg, 1.28 mmol), (prepared as described for the starting material in Example 10), in DMF (6 ml). After stirring overnight at 40° C. the mixture was diluted with water and adjusted to pH7. After extraction with ethyl acetate the organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The residue was purified by flash chromatography using methylene chloride/methanol (98/2) as eluent to give 4-chloro-6-methoxy-7-[(1-methylimidazol-2-yl)methoxy]cinnoline (111 mg, 29%).

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