反応 #48846

反応方程式

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

収率 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

収率 62.1%

溶媒

DCM

反応条件

後処理

1. 1
   ろ過The reaction mixture was filtered through celite
2. 2
   洗浄washed with DCM (2×50 mL)
3. 3
   その他The DCM was removed in vacuo
4. 4
   その他the residual oil partitioned between ethyl acetate (100 mL) and water (100 mL)
5. 5
   ろ過filtered
6. 6
   洗浄the ethyl acetate layer washed with brine (50 mL)
7. 7
   乾燥dried (MgSO4)
8. 8
   その他evaporated to a residue which
9. 9
   その他was chromatographed on silica
10. 10
    洗浄eluting with a gradient of 50-100% ethyl acetate in isohexane

実験手順

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).

出典