Potassium Carbonate → 1h-Pyrazole-3-carboxamide,4-iodo-1-[(4-methoxyphenyl)methyl]-n-phenyl-

HRID 1624970Notes

Reaction equation

HRID 1624970 reaction equation
[C:1]1([NH:7][C:8]([C:10]2[C:14]([I:15])=[CH:13][NH:12][N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>C(#N)C>[C:1]1([NH:7][C:8]([C:10]2[C:14]([I:15])=[CH:13][N:12]([CH2:28][C:27]3[CH:30]=[CH:31][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[N:11]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178521931HCID 178521931, compound

Product 1

HCID 668573141h-Pyrazole-3-carboxamide,4-iodo-1-[(4-methoxyphenyl)methyl]-n-phenyl-Yield 71.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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.

Workup

  1. customthen evaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and brine
  3. customthe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was purified by flash column chromatography
  8. washeluting with 1:3 ethyl acetate/hexane
  9. additionthe product containing fractions
  10. customevaporated

Sources & evidence

ORD record
ord-5409fe083823415fa4982c54406ff9c6
Source dataset
uspto-grants-2014_07
Patent number
US08779147B2

Reaction notes

Loading…