تفاعل #48846

معادلة التفاعل

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

المردود 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

المردود 62.1%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction mixture was filtered through celite
2. 2
   غسيلwashed with DCM (2×50 mL)
3. 3
   أخرىThe DCM was removed in vacuo
4. 4
   أخرىthe residual oil partitioned between ethyl acetate (100 mL) and water (100 mL)
5. 5
   ترشيحfiltered
6. 6
   غسيلthe ethyl acetate layer washed with brine (50 mL)
7. 7
   تجفيفdried (MgSO4)
8. 8
   أخرىevaporated to a residue which
9. 9
   أخرىwas chromatographed on silica
10. 10
    غسيلeluting with a gradient of 50-100% ethyl acetate in isohexane

الإجراء التجريبي

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).

المصدر