Reacción #329375

Ecuación de reacción

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

Rendimiento 99.0%

Disolventes

acetic

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was transferred to a round bottom flask
2. 2
   Otroevaporated
3. 3
   workup.ADDITIONtoluene was added
4. 4
   Otroagain evaporated
5. 5
   workup.ADDITIONCH2Cl2 and silica was finally added
6. 6
   Otrothe mixture was evaporated to dryness
7. 7
   OtroPurification

Procedimiento

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.

Fuente