反応 #706797
ord-b86d58c6df5441589df6945e10a4a6e9
反応方程式
反応物
反応条件
後処理
- 1温度The resulting solution was warmed to room temperature
- 2温度This solution was heated to 50° C. for 2 hours
- 3温度cooled to room temperature
- 4その他the reaction quenched by the addition of saturated aqueous NH4Cl
- 5抽出Thei solution was extracted with EtOAc
- 6洗浄the combined organic layers washed with H2O and saturated aqueous NaCl
- 7乾燥before being dried (MgSO4)
- 8濃縮concentrated under reduced pressure
実験手順
A solution of 2-methylthiophene (130.0 mg, 1.30 mmol) in 2.0 mL of THF was cooled to -78° C. and n-butyllithium (83.3 mg, 1.30 mmol, 0.84 ml of a 1.6M solution in hexanes) was added and the solution warmed to 0° C. during 1.5 hours. A solution of ZnCl2 (341.0 mg, 2.50 mmol) in 3.0 mL THF was slowly added via cannula. The resulting solution was warmed to room temperature, stirred for 40 minutes, and transferred via cannula to a solution of ethyl 4-[(2,2-dimethyl-4-trifluoromethanesulfonyloxy-7-fluoro-(2H)-thiochromen-6-yl)ethynyl]-benzoate (Compound 211, 158.0 mg, 0.31 mmol) and tetrakis(triphenylphosphine) palladium(0) (24.0 mg, 0.02 mmol) in 2.0 mL THF. This solution was heated to 50° C. for 2 hours, cooled to room temperature, and the reaction quenched by the addition of saturated aqueous NH4Cl. Thei solution was extracted with EtOAc and the combined organic layers washed with H2O and saturated aqueous NaCl before being dried (MgSO4) and concentrated under reduced pressure. The title compound, 70.0 mg (50%), was isolated by column chromatography (3% EtOAc/hexanes) as a waxy solid. 1H NMR (300 MHz, CDCl3) δ:8.01 (2H, d, J=8.3 Hz), 7.61 (1H, d, J=7.5 Hz), 7.58 (2H, d, J=8.3 Hz), 7.13 (1H, d, J=7.2 Hz), 6.82 (1H, d, J=4.4 Hz), 6.73 1H, d, J=4.4 Hz), 5.96 (1H, s), 4.39 (2H, q, J=7.1 Hz), 2.52 (3H, s), 1.46 (6H, s), 1.41 (3H, t, J=7.1 Hz).