تفاعل #2048296

معادلة التفاعل

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

potassium carbonate

trimethylboroxin

→

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

المردود 56.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was partitioned between H2O-DCM
2. 2
   غسيلthe aqueous phase was washed several times with DCM
3. 3
   تجفيفThe combined organic fractions were dried over Na2SO4
4. 4
   تركيزconcentrated
5. 5
   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, 0.911 mmol), potassium carbonate (630 mg, 4.56 mmol), PdCl2(dppf) (66.7 mg, 0.091 mmol) and trimethylboroxin (0.25 ml, 1.82 mmol) in N,N-dimethylformamide (9.1 ml) was stirred at 110° C. in a sealed tube for 2 h. The reaction mixture was 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-(1,4-dimethyl-1H-pyrazol-5-yl)-5-ethyl-2-thiophenecarboxylate (143 mg, 0.51 mmol, 56% yield) as a yellow oil: LCMS (ES) m/z=265 (M+H)+.

المصدر