تفاعل #706797
ord-b86d58c6df5441589df6945e10a4a6e9
معادلة التفاعل
المتفاعلات
ظروف التفاعل
المعالجة
- 1درجة الحرارةThe resulting solution was warmed to room temperature
- 2درجة الحرارةThis solution was heated to 50° C. for 2 hours
- 3درجة الحرارةcooled to room temperature
- 4أخرىthe reaction quenched by the addition of saturated aqueous NH4Cl
- 5استخلاصThei solution was extracted with EtOAc
- 6غسيلthe combined organic layers washed with H2O and saturated aqueous NaCl
- 7تجفيفbefore being dried (MgSO4)
- 8تركيزconcentrated under reduced pressure
الإجراء التجريبي
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).