Reaction #48600

Reaction equation

4-methoxybenzyl chloride

4-iodo-1H-pyrazole-3-carboxylic acid phenylamide

potassium carbonate

→

4-iodo-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide

Yield 71.2%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Otherthen evaporated under reduced pressure
2. 2
   OtherThe residue was 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 was purified by flash column chromatography
8. 8
   Washeluting with 1:3 ethyl acetate/hexane
9. 9
   workup.ADDITIONthe product containing fractions
10. 10
    Otherevaporated

Procedure

A solution of 4-iodo-1H-pyrazole-3-carboxylic acid phenylamide (670 mg; 2.14 mmol) in acetonitrile (10 ml) was treated with potassium carbonate (360 mg; 2.57 mmol)) followed by 4-methoxybenzyl chloride (320 μl; 2.35 mmol). The mixture was stirred at room temperature overnight then evaporated under reduced pressure. The residue was partitioned between ethyl acetate and brine; the ethyl acetate layer was separated, dried (MgSO4), filtered and evaporated. The crude material was purified by flash column chromatography eluting with 1:3 ethyl acetate/hexane and the product containing fractions combined and evaporated to give 660 mg of 4-iodo-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide.

Source