Réaction #48601

Équation de réaction

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

potassium carbonate

3-(hydroxymethyl)benzene boronic acid

→

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

Rendement 131.9%

Solvants

ethanol toluene water

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was evaporated
2. 2
   Autrethe residue partitioned between ethyl acetate and brine
3. 3
   AutreThe ethyl acetate layer was separated
4. 4
   Séchagedried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Autreevaporated
7. 7
   Autrethe crude material purified by flash column chromatography
8. 8
   Lavageeluting with 1:2
9. 9
   workup.ADDITIONProduct containing fractions
10. 10
    Autreevaporated

Mode opératoire

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-(hydroxymethyl)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.

Source