Реакция #8588

Уравнение реакции

1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone

N,N-dimethylformamide dimethyl acetal

ethylacetate

water

→

(2E)-1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one

Выход 99.0%

Условия реакции

Обработка

1. 1
   Температураto reflux for 6 days
2. 2
   ПромывкаThe organic layer was washed with brine
3. 3
   ЭкстракцияThe aqueous layer was extracted with ethyl acetate
4. 4
   Сушкаthe combined organics were dried over magnesium sulfate
5. 5
   ФильтрацияFiltration and concentration

Методика

A solution of 1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone (3.1 g, 9.2 mmol) in N,N-dimethylformamide dimethyl acetal (25 mL) was heated to reflux for 6 days. The mixture was cooled to room temperature, ethylacetate was added followed by water. The organic layer was washed with brine. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over magnesium sulfate. Filtration and concentration followed by flash chromatography (ethyl acetate) provided (2E)-1-[7-(cyclopentylamino)-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]-3-(dimethylamino)-2-propen-1-one (3.6 g, 99%) as a tinted oil. 1H NMR (CDCl3): δ 7.73–7.61 (m, 4 H), 7.32 (t, 1 H), 7.14 (t, 2 H), 6.03 (d, 1 H), 5.96 (d, 1 H), 5.05 (d, 1 H), 3.99 (m, 1 H), 5.15–2.42 (broad, 6 H), 2.19–2.08 (m, 2 H), 1.86–1.62 (m, 6 H); 19F NMR (CDCl3) δ −113.75; MS m/ 393 (M+1).

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