Reaction #48601

Reaction equation

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

Yield 131.9%

Solvents

ethanol toluene water

Conditions

Workup

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

Procedure

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