تفاعل #651654

معادلة التفاعل

[3-(hydroxymethyl)phenyl]boronic acid (1,1-dimethylethyl)(trimethyl)silane

PPh3

K2CO3

1,1-dimethylethyl [(3-bromo-4-cyanophenyl)methyl]carbamate

→

product

1,1-Dimethylethyl {[3′-({[(1,1-dimethylethyl)(methyl)silyl]oxy}methyl)-6-methyl-3-biphenylyl]methyl}carbamate ethane

المذيبات

1,4-dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter cooled to room temperature
2. 2
   أخرىthe solvent was removed under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2 (50 mL)
4. 4
   غسيلwashed with water (20 mL), brine (20 mL)
5. 5
   تجفيفdried over Na2SO4
6. 6
   أخرىAfter the solvent was removed
7. 7
   أخرىthe crude product was purified on Al2O3 column chromatography
8. 8
   غسيلeluting with CH2Cl2

الإجراء التجريبي

Pd(OAc)2 (56.3 mg, 0.25 mmol), PPh3 (263.0 mg, 1.0 mmol), K2CO3 (1.7 g, 12.5 mmol) and 1,1-dimethylethyl [(3-bromo-4-cyanophenyl)methyl]carbamate (2.6 g, 8.4 mmol) were suspended in 1,4-dioxane (30 mL). After the mixture was heated to 80° C. for 15 min, [3-(hydroxymethyl)phenyl]boronic acid-(1,1-dimethylethyl)(trimethyl)silane (2.7 g, 10.0 mmol) was added. Then the reaction mixture was stirred over night at 100° C. After cooled to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (50 mL), then washed with water (20 mL), brine (20 mL), and dried over Na2SO4. After the solvent was removed, the crude product was purified on Al2O3 column chromatography, eluting with CH2Cl2. 2.6 g of the product, 1,1-dimethylethyl{[3′-({[(1,1-dimethylethyl)(methyl)silyl]oxy}methyl)-6-methyl-3-biphenylyl]methyl}carbamate-ethane, was obtained (yield: 60%). 1H NMR (400 MHz, CDCl3): δ 0.12 (s, 6 H), 0.95 (s 9 H), 1.46 (s, 9 H), 4.41-4.42 (m, 2 H), 4.81 (s, 2 H), 7.37-7.47 (m, 6 H), 7.71 (d, J=8.0 Hz, 1 H); 13C NMR (100 MHz, CDCl3): δ −5.3, 18.4, 25.9, 28.3, 44.2, 64.7, 80.0, 109.9, 118.6, 126.1, 126.2, 126.4, 127.3, 128.6, 134.0, 137.9, 142.0, 144.5, 145.8, 155.8; HPLC: retention time: 9.500 min; purity: 95.2% (HPLC).

المصدر