تفاعل #48601

معادلة التفاعل

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

المردود 131.9%

المذيبات

ethanol toluene water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was evaporated
2. 2
   أخرىthe residue partitioned between ethyl acetate and brine
3. 3
   أخرىThe ethyl acetate layer was separated
4. 4
   تجفيفdried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   أخرىevaporated
7. 7
   أخرىthe crude material purified by flash column chromatography
8. 8
   غسيلeluting with 1:2
9. 9
   workup.ADDITIONProduct containing fractions
10. 10
    أخرىevaporated

الإجراء التجريبي

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.

المصدر