Reacción #48846

Ecuación de reacción

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

Rendimiento 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

Rendimiento 62.1%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction mixture was filtered through celite
2. 2
   Lavadowashed with DCM (2×50 mL)
3. 3
   OtroThe DCM was removed in vacuo
4. 4
   Otrothe residual oil partitioned between ethyl acetate (100 mL) and water (100 mL)
5. 5
   Filtraciónfiltered
6. 6
   Lavadothe ethyl acetate layer washed with brine (50 mL)
7. 7
   Secadodried (MgSO4)
8. 8
   Otroevaporated to a residue which
9. 9
   Otrowas chromatographed on silica
10. 10
    Lavadoeluting with a gradient of 50-100% ethyl acetate in isohexane

Procedimiento

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).

Fuente