تفاعل #1932711

معادلة التفاعل

methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate

potassium carbonate

1,4-dioxane

→

methyl 4-(4-ethenyl-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate

المردود 73.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction contents
2. 2
   أخرىwere partitioned between H2O-DCM
3. 3
   غسيلthe aqueous phase was washed several times with DCM
4. 4
   تجفيفThe combined organic fractions were dried over Na2SO4
5. 5
   تركيزconcentrated
6. 6
   أخرىpurified via column chromatography (10-50% EtOAc in hexanes)

الإجراء التجريبي

A solution of methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate (300 mg, 0.91 mmol), potassium carbonate (630 mg, 4.56 mmol), bis(tri-t-butylphosphine)palladium(0) (23 mg, 0.05 mmol) and 2,4,6-trivinylcycloboroxane-pyridine complex (110 mg, 0.46 mmol) in 1,4-dioxane (5 ml) and water (1 ml) was stirred at 80° C. in a sealed tube for 2 h. The reaction contents were partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (10-50% EtOAc in hexanes) affording methyl 4-(4-ethenyl-1-methyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate (187 mg, 0.66 mmol, 73% yield) as a clear oil: LCMS (ES) m/z=277 (M+H)+.

المصدر