反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 77 °C
PROCEDURE
实验过程
Following the procedure described in Step 1 of Example 1, 2-{[1-bromo-6-(3-pentanoyl-1-benzofuran-2-yl)-2-naphthyl]oxy}acetonitrile (0.476 g, 1.03 mmol) was coupled to 4-trifluoromethylphenylboronic acid (0.785 g, 4.13 mmol), using [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.088 g, 0.108 mmol) and potassium carbonate (0.301 g, 2.18 mmol) in dioxane (10 mL) and water (1 mL). The reaction mixture was heated at 77° C. for 16 hours. Purification by flash chromatography (Biotage apparatus) using 2-10% ethyl acetate in hexane as an eluant yielded 2-({6-(3-pentanoyl-1-benzofuran-2-yl)-1-[4-(trifluoromethyl)phenyl]-2-naphthyl}oxy)acetonitrile as a yellow wax (0.364 g); 1HNMR (300 MHz, DMSO-d6): δ8.55 (s, 1H), 8.35 (d, 1H, J=8.5 Hz), 8.05 (d, 1H, J=7.7 Hz), 7.95 (d, 2H, J=7.7 Hz), 7.75-7.85 (m, 2H), 7.75 (d, 1H, J=7.7 Hz), 7.35-7.5 (m, 3H), 5.3 (s, 2H), 2.75 (t, 2H, J=7.7 Hz), 1.5-1.6 (m, 2H), 1.1-1.25 (m, 2H), and 0.7 (t, 3H, J=7.7 Hz).
WORKUP
后处理
- customPurification by flash chromatography (Biotage apparatus)