반응 #48601

반응 방정식

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

수율 131.9%

용매

ethanol toluene water

반응 조건

후처리

1. 1
   기타The reaction was evaporated
2. 2
   기타the residue partitioned between ethyl acetate and brine
3. 3
   기타The ethyl acetate layer was separated
4. 4
   건조dried (MgSO4)
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타the crude material purified by flash column chromatography
8. 8
   세척eluting with 1:2
9. 9
   workup.ADDITIONProduct containing fractions
10. 10
    기타evaporated

실험 절차

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.

출처