反応 #48601

反応方程式

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

収率 131.9%

溶媒

ethanol toluene water

反応条件

後処理

1. 1
   その他The reaction was evaporated
2. 2
   その他the residue partitioned between ethyl acetate and brine
3. 3
   その他The ethyl acetate layer was separated
4. 4
   乾燥dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   その他evaporated
7. 7
   その他the crude material purified by flash column chromatography
8. 8
   洗浄eluting with 1:2
9. 9
   workup.ADDITIONProduct containing fractions
10. 10
    その他evaporated

実験手順

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.

出典