Reacción #219243

Ecuación de reacción

4-iodo-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide

potassium carbonate

→

4-(3-hydroxymethyl-phenyl)-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide

Disolventes

ethanol toluene water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was evaporated
2. 2
   Otrothe residue partitioned between ethyl acetate and brine
3. 3
   OtroThe ethyl acetate layer was separated
4. 4
   Secadodried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Otroevaporated
7. 7
   Otrothe crude material purified by flash column chromatography
8. 8
   Lavadoeluting with 1:2
9. 9
   workup.ADDITIONProduct containing fractions
10. 10
    Otroevaporated

Procedimiento

A mixture of 4-iodo-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide (50 mg; 0.11 mmol), bis(tri-tert-butylphosphine)palladium (12 mg), potassium carbonate (100 mg; 0.66 mmol) and 3-(hydroxmethyl)benzene boronic acid (21 mg; 0.14 mmol) in ethanol/toluene/water (4 ml:1 ml:1 ml) was heated at 120° C. (50 W) for 15 minutes in a CEM Discover microwave synthesiser. The reaction was evaporated and the residue partitioned between ethyl acetate and brine. The ethyl acetate layer was separated, dried (MgSO4), filtered and evaporated and the crude material purified by flash column chromatography eluting with 1:2 then 2:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 60 mg of 4-(3-hydroxymethyl-phenyl)-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide.

Fuente