تفاعل #8588

معادلة التفاعل

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

المردود 99.0%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto reflux for 6 days
2. 2
   غسيلThe organic layer was washed with brine
3. 3
   استخلاصThe aqueous layer was extracted with ethyl acetate
4. 4
   تجفيفthe combined organics were dried over magnesium sulfate
5. 5
   ترشيحFiltration and concentration

الإجراء التجريبي

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).

المصدر