Реакция #48846

Уравнение реакции

3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

4-ethoxycarbonylphenylboronic acid

triethylamine

→

desired compound

Выход 62.1%

Ethyl 4-(3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoate

Выход 62.1%

Растворители

DCM

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction mixture was filtered through celite
2. 2
   Промывкаwashed with DCM (2×50 mL)
3. 3
   ДругоеThe DCM was removed in vacuo
4. 4
   Другоеthe residual oil partitioned between ethyl acetate (100 mL) and water (100 mL)
5. 5
   Фильтрацияfiltered
6. 6
   Промывкаthe ethyl acetate layer washed with brine (50 mL)
7. 7
   Сушкаdried (MgSO4)
8. 8
   Другоеevaporated to a residue which
9. 9
   Другоеwas chromatographed on silica
10. 10
    Промывкаeluting with a gradient of 50-100% ethyl acetate in isohexane

Методика

A suspension of 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (4.5 g, 0.011 mol), 4-ethoxycarbonylphenylboronic acid (3.24 g, 0.016-mol), copper (II) acetate (3.06 g, 0.016 mol), triethylamine (7.74 mL, 0.055 mol) and freshly activated 4 Å molecular sieves (13 g) in DCM (180 mL) was stirred at ambient temperature and under ambient atmosphere for 3 days. The reaction mixture was filtered through celite, washed with DCM (2×50 mL). The DCM was removed in vacuo and the residual oil partitioned between ethyl acetate (100 mL) and water (100 mL), filtered and the ethyl acetate layer washed with brine (50 mL), dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 50-100% ethyl acetate in isohexane, to give the desired compound (3.78 g).

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