Reaktion #329375

Reaktionsgleichung

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

Ausbeute 99.0%

Lösungsmittel

acetic

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was transferred to a round bottom flask
2. 2
   Sonstigeevaporated
3. 3
   workup.ADDITIONtoluene was added
4. 4
   Sonstigeagain evaporated
5. 5
   workup.ADDITIONCH2Cl2 and silica was finally added
6. 6
   Sonstigethe mixture was evaporated to dryness
7. 7
   SonstigePurification

Vorschrift

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.

Quelle