Methyl iodide → HCID 66985987, compound

HRID 1254022Notes

Reaction equation

HRID 1254022 reaction equation
I[C:2]1[N:6]([CH3:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[N:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[O:21][CH:22]=NN=2)=[CH:16][CH:15]=1.C([O-])([O-])=[O:26].[Cs+].[Cs+].CI>C1COCC1>[CH3:7][N:6]1[CH:2]=[C:3]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:21][CH3:22])=[O:26])=[CH:16][CH:15]=2)[N:4]=[C:5]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 58497206HCID 58497206, compound

Product 1

HCID 66985987HCID 66985987, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-(2-pyridin-2-yl-1H-imidazol-4-yl)benzoate (from Step 1, 19.55 g, 70 mmol) was dissolve in THF (160 mL), to which was added Cs2CO3 (29.6 g, 91 mmol) at 0° C. After stirring for 5 min, MeI (11 mL, 175 mmol) was added. After stirring overnight at rt, the reaction was quenched with aq NH4Cl. The product was extracted with EtOAc and the organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated. The residue was subject to silica column chromatography (0-20% EtOAc in hexanes) to give 12.5 g of methyl 4-(1-methyl-2-pyridin-2-yl-1H-imidazol-4-yl)benzoate. LCMS: m/z 294 (M+H)+.

Workup

  1. stirringAfter stirring overnight at rt
  2. customthe reaction was quenched with aq NH4Cl
  3. extractionThe product was extracted with EtOAc
  4. washthe organic layer was washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-736d89d74c474d4cba31b76250212934
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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