Реакция #48827

Уравнение реакции

tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

triethylamine

→

oil

Выход 39.0%

tert-Butyl 3-({3-[4-(ethoxycarbonyl)phenoxy]-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate

Выход 39.0%

Растворители

DCM

Условия реакции

Обработка

1. 1
   Другоеfor 7 hours
2. 2
   ДругоеReaction mixture
3. 3
   Фильтрацияfiltered through diatomaceous earth
4. 4
   Промывкаwas washed with DCM (×3)
5. 5
   КонцентрированиеFiltrate concentrated in vacuo
6. 6
   Промывкаwashed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine
7. 7
   Сушкаdried (MgSO4)
8. 8
   ФильтрацияFiltered
9. 9
   Концентрированиеfiltrate concentrated in vacuo
10. 10
    Другоеchromatographed (0-50% ethyl acetate/isohexane)

Методика

tert-Butyl 3-({3-hydroxy-5-[(1S)-2-methoxy-1-methylethoxy]benzoyl}amino)-1H-pyrazole-1-carboxylate (391 mg, 1 mmol), ethyl-4-boronic acid benzoate (388 mg, 2.0 equiv), copper (II) acetate (363 mg, 2.0 equiv) and triethylamine (0.7 mL; 5.0 equiv) were suspended in dry DCM over freshly activated powdered 4A molecular sieves (ca. 1 g) for 7 hours under an ambient atmosphere. Reaction mixture filtered through diatomaceous earth was washed with DCM (×3). Filtrate concentrated in vacuo, taken up in ethyl acetate and washed with 1M hydrochloric acid, saturated sodium hydrogen carbonate, saturated brine and dried (MgSO4). Filtered, filtrate concentrated in vacuo and chromatographed (0-50% ethyl acetate/isohexane) to give a brown oil (210 mg, 39%).

Источник