Реакция #329375

Уравнение реакции

5-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

acetonylacetone

EtOAc

→

5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

Выход 99.0%

Растворители

acetic

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was transferred to a round bottom flask
2. 2
   Другоеevaporated
3. 3
   workup.ADDITIONtoluene was added
4. 4
   Другоеagain evaporated
5. 5
   workup.ADDITIONCH2Cl2 and silica was finally added
6. 6
   Другоеthe mixture was evaporated to dryness
7. 7
   ДругоеPurification

Методика

A solution of 5-amino-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (100 mg, 0.43 mmol) and acetonylacetone (507 μL, 4.31 mmol) in glacial acetic (3 mL) acid was heated at 140° C. in the micro for 30 min. The mixture was transferred to a round bottom flask using EtOAc and evaporated, toluene was added and again evaporated, CH2Cl2 and silica was finally added and the mixture was evaporated to dryness. Purification using silica chromatography (short plug) gave 5-(2,5-dimethyl-1H-pyrrol-1-yl)-1-(2-fluoro-4-hydroxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (132 mg, 99%) as a 1:1 mixture with the starting material acetonylacetone. The product was used as such in the next step.

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