تفاعل #1932819

معادلة التفاعل

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

potassium carbonate

trimethylboroxine

→

title compound

المردود 96.0%

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

المردود 96.0%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   تركيزThis reaction mixture was concentrated
2. 2
   أخرىpartitioned 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 (635 mg, 1.93 mmol), potassium carbonate (1.33 g, 9.64 mmol), PdCl2(dppf) (141 mg, 0.19 mmol) and trimethylboroxine (0.54 ml, 3.86 mmol) in N,N-dimethylformamide (3 ml) was stirred at 110° C. in a sealed tube for 2 h. This reaction mixture was concentrated and partitioned between H2O-DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (10-50% EtOAc in hexanes) affording the title compound (488 mg, 96%) as a yellow oil: LCMS (ES) m/e 265 (M+H)+.

المصدر