Water → HCID 59260059, compound

HRID 642988Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9]C=[C:11](C(O)=O)[N:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].I[CH3:19].O.C[CH2:22][O:23][C:24]([CH3:26])=[O:25]>CN(C=O)C>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:11])[CH:19]=[C:26]([C:24]([O:23][CH3:22])=[O:25])[N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 2-(4-iodophenyl)-1H-imidazole-4-carboxylic acid prepared above (257 mg, 0.818 mmol) and NaH (60% suspension, washed with hexane, 82 mg, 2.1 mmol) in DMF (8 mL) was added iodomethane (0.130 mL, 2.1 mmol). The mixture was heated at 50° C. for 2 h. More iodomethane (0.100 mL) was added to the reaction mixture. After being stirred at 50° C. for an additional 2 h, water and EtOAc were added. The organic layer was separated, dried over Na2SO4, concentrated in vacuo to give methyl 2-(4-iodophenyl)-1-methyl-1H-imidazole-4-carboxylate (152 mg). MS 342.8 (M+H).

Workup

customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-ee22c4ce7ce748e8a5bb47875a572641
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696352B2

Reaction notes

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