반응 #48846

반응 방정식

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

수율 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

수율 62.1%

용매

DCM

반응 조건

후처리

1. 1
   여과The reaction mixture was filtered through celite
2. 2
   세척washed with DCM (2×50 mL)
3. 3
   기타The DCM was removed in vacuo
4. 4
   기타the residual oil partitioned between ethyl acetate (100 mL) and water (100 mL)
5. 5
   여과filtered
6. 6
   세척the ethyl acetate layer washed with brine (50 mL)
7. 7
   건조dried (MgSO4)
8. 8
   기타evaporated to a residue which
9. 9
   기타was chromatographed on silica
10. 10
    세척eluting with a gradient of 50-100% ethyl acetate in isohexane

실험 절차

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).

출처