Cesium carbonate → 4-(4-Nitro-imidazol-1-yl)-benzoic acid methyl ester

HRID 1714281Notes

Reaction equation

HRID 1714281 reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].I[C:10]1[CH:18]=[CH:17][C:13]([C:14]([O-:16])=[O:15])=[C:12](C)[CH:11]=1.[C:20](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[O-]S(C(F)(F)F)(=O)=O.[Cu+]>[CH3:20][O:16][C:14](=[O:15])[C:13]1[CH:17]=[CH:18][C:10]([N:7]2[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[CH:6]2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 226178964-Iodo-methylbenzoateHCID 178526856HCID 178526856, compound

Product 1

HCID 671649044-(4-Nitro-imidazol-1-yl)-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 9813164Copper(I) trifluoromethanesulfonateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-nitroimidazole (1 equiv) was combined with 4-iodo-methylbenzoate (1.2 equiv), cesium carbonate (1.0 equiv), copper (I) triflate (0.05 equiv), in DMF and heated overnight at 100° C. The solid was filtered and washed with methylene chloride, the resultant solvent was concentrated, and residue purified by silica gel chromatography to provide the title compound: MS m/z 248.2 (M+1).

Workup

  1. filtrationThe solid was filtered
  2. washwashed with methylene chloride
  3. concentrationthe resultant solvent was concentrated
  4. customresidue purified by silica gel chromatography

Sources & evidence

ORD record
ord-75e299f5a89143aa81ec61b75c368edb
Source dataset
uspto-grants-2010_09
Patent number
US07795447B2

Reaction notes

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