反应详情

温度

80 °C

Pd(OAc)2 (88.9 mg, 0.39 mmol), PPh3 (415.0 mg, 1.6 mmol), K2CO3 (2.7 g, 19.8 mmol) and 1,1-dimethylethyl [(3-bromo-2-fluorophenyl)methyl]carbamate (4.0 g, 13.2 mmol) were suspended in 1,4-dioxane (50 mL). After the mixture was heated to 80° C. for 15 min, [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (4.2 g, 15.8 mmol) was added. Then the reaction mixture was stirred over night at 100° C. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (80 mL), then was washed with water (30 mL), brine (30 mL), and dried over Na2SO4. After the solvent was removed, the crude product was purified on an Al2O3 column chomatography, eluting with PE/EA (20:1). 1,1-Dimethylethyl {[3′-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylyl]methyl}carbamate, was obtained (1.98 g, yield: 34%). 1H NMR (400 MHz, CDCl3) δ 0.12 (s, 6H), 0.95 (s, 9H), 4.42-4.43 (m, 2H), 4.80 (s, 2H), 4.96 (s, 1H), 7.17-7.48 (m, 7H); 13C NMR (400 MHz, CDCl3) δ −5.3, 18.4, 25.9, 28.3, 38.9, 64.8, 124.2, 125.4, 126.7, 127.6, 128.3, 128.7, 129.7, 129.2, 129.7, 135.4, 141.6, 155.8; HPLC: retention time: 4.630 min; purity: 99.4% (HPLC).

1. temperatureAfter cooling to room temperature
2. customthe solvent was removed under reduced pressure
3. dissolutionThe residue was dissolved in CH2Cl2 (80 mL)
4. washwas washed with water (30 mL), brine (30 mL)
5. dry with materialdried over Na2SO4
6. customAfter the solvent was removed
7. customthe crude product was purified on an Al2O3 column chomatography
8. washeluting with PE/EA (20:1)