تفاعل #651665

معادلة التفاعل

1,1-Dimethylethyl [(3-bromo-5-cyanophenyl)methyl]carbamate

PPh3

K2CO3

[3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid

→

1,1-Dimethylethyl {[5-cyano-3′-({[dimethyl(1-methylethyl)silyl]oxy}methyl)-3-biphenylyl]methyl}carbamate ethane

المردود 72.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture reaction
2. 2
   درجة الحرارةat reflux overnight
3. 3
   أخرىThe solvent was removed under reduced pressure
4. 4
   workup.ADDITIONdiluted with CH2Cl2 (100 mL)
5. 5
   غسيلThe organic layer was washed with water (30 mL) and brine (30 mL)
6. 6
   تجفيفAnd the organic layer was dried over Na2SO4
7. 7
   أخرىThe product 1,1-dimethylethyl {[5-cyano-3′-({[dimethyl(1-methylethyl)silyl]oxy}methyl)-3-biphenylyl]methyl}carbamate-ethane (2.0 g) was purified by flash column chromatography

الإجراء التجريبي

1,1-Dimethylethyl [(3-bromo-5-cyanophenyl)methyl]carbamate (1.90 g, 6.11 mmol), Pd(OAc)2 (76 mg), PPh3 (228 mg) and K2CO3 (1.27 g, 9.16 mmol) were dissolved in dioxane (50 mL). The mixture was heated at 70° C. for 30 min, and then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (2.11 g, 7.94 mmol) was added. The mixture reaction was stirred at reflux overnight. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (30 mL) and brine (30 mL). And the organic layer was dried over Na2SO4. The product 1,1-dimethylethyl {[5-cyano-3′-({[dimethyl(1-methylethyl)silyl]oxy}methyl)-3-biphenylyl]methyl}carbamate-ethane (2.0 g) was purified by flash column chromatography. Yield: 72%. 1H NMR (400 MHz, CDCl3): δ 0.12 (s, 6 H), 0.96 (s, 9 H), 1.47 (s, 9 H), 4.41 (d, J=6 Hz, 2 H), 4.81 (s, 2 H), 7.38-7.44 (m, 3 H), 7.50 (s, 1 H), 7.55 (s, 1 H), 7.70 (s, 1 H), 7.75 (s, 1H); 13C NMR (100 MHz, CDCl3): δ −5.2, 18.4, 25.9, 28.3, 43.4, 64.7, 80.1, 113.1, 118.7, 124.7, 125.6, 126.1, 129.0, 129.2, 129.6, 130.4, 133.4, 134.8, 138.6, 141.2, 142.5, 142.9, 155.9; HPLC: retention time: 4.670 min; purity: 94.4%; MS: m/z 453 (M+, 32), 339 (M+−TBS, 100).

المصدر