Reaktion #48601

Reaktionsgleichung

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

Ausbeute 131.9%

Lösungsmittel

ethanol toluene water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle