Реакция #48601

Уравнение реакции

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

Выход 131.9%

Растворители

ethanol toluene water

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was evaporated
2. 2
   Другоеthe residue partitioned between ethyl acetate and brine
3. 3
   ДругоеThe ethyl acetate layer was separated
4. 4
   Сушкаdried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated
7. 7
   Другоеthe crude material purified by flash column chromatography
8. 8
   Промывкаeluting with 1:2
9. 9
   workup.ADDITIONProduct containing fractions
10. 10
    Другоеevaporated

Методика

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.

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