反应详情

温度

80 °C

To a solution of N-(2-bromo-3-fluorophenyl)butyramide (2.0 g, 7.0 mmol) in Et3N (100 mL) was added 4,4-dimethylpent-2-yne (6.0 g, 60 mmol), CuI (70 mg, 3.8 mmol), and Pd(PPh3)2Cl2 (500 mg) successively at room temperature under N2. The mixture was heated at 80° C. overnight. The cooled mixture was filtered and the filtrate was extracted with EtOAc (40 mL×3). The organic layers were washed with sat. NaCl, dried over anhydrous Na2SO4, and evaporated under vacuum. The crude compound was purified by column chromatography on silica gel (10% EtOAc in petroleum ether) to give N-(2-(3,3-dimethylbut-1-ynyl)-3-fluorophenyl)butyramide (1.1 g, 55%). NMR (400 MHz, CDCl3) δ 8.20 (d, J=7.6, 1 H), 7.95 (s, 1 H), 7.21 (m, 1 H), 6.77 (t, J=7.6 Hz, 1 H), 2.39 (t, J=7.6 Hz, 2 H), 1.82-1.75 (m, 2H), 1.40 (s, 9 H), 1.12 (t, J=7.2 Hz, 3 H).

1. filtrationThe cooled mixture was filtered
2. extractionthe filtrate was extracted with EtOAc (40 mL×3)
3. washThe organic layers were washed with sat. NaCl
4. dry with materialdried over anhydrous Na2SO4
5. customevaporated under vacuum
6. customThe crude compound was purified by column chromatography on silica gel (10% EtOAc in petroleum ether)