Reaktion #48846

Reaktionsgleichung

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

Ausbeute 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

Ausbeute 62.1%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered through celite
2. 2
   Waschenwashed with DCM (2×50 mL)
3. 3
   SonstigeThe DCM was removed in vacuo
4. 4
   Sonstigethe residual oil partitioned between ethyl acetate (100 mL) and water (100 mL)
5. 5
   Filtrationfiltered
6. 6
   Waschenthe ethyl acetate layer washed with brine (50 mL)
7. 7
   Trocknendried (MgSO4)
8. 8
   Sonstigeevaporated to a residue which
9. 9
   Sonstigewas chromatographed on silica
10. 10
    Wascheneluting with a gradient of 50-100% ethyl acetate in isohexane

Vorschrift

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).

Quelle