Dimethylformamide → 2-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

HRID 2293510Notes

Reaction equation

HRID 2293510 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:4]=[CH:3]1.C([Li])CCC.CN([CH:27]=[O:28])C>C1COCC1>[CH:27]([C:3]1[N:2]([CH3:1])[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[C:5]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:4]=1)=[O:28]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 187714831-Methyl-4-phenyl-5-(4-pyridyl)imidazoleHCID 178418339Butyllithium

Product 1

HCID 187715342-Formyl-1-methyl-4-phenyl-5-[4-pyridyl]imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-methyl-4-phenyl-5-[4-pyridinyl]imidazole (0.275 g, 1.17 mmol) in THF at -78° C. was added n-butyllithium (0.56 mL of 2.5M solution, 1.40 mmol). The resulting red-orange solution was allowed to stir at -78° C. for 0.5 h when DMF (0.18 mL, 2.34 mmol) was added. The mixture was allowed to warm to rt and stir for 4 h, then quenched with ice water and partitioned between CH2Cl2 and H2O. The organic extract was washed with aqueous NaCl and dried (MgSO4). The solvent was removed in vacuo and the residue was purified by flash chromatography eluting with 50:1 CH2Cl2 /MeOH. The title compound was obtained as a white solid (0.187 g, 61%): mp 167°-168° C.

Workup

  1. additionwas added
  2. customquenched with ice water
  3. custompartitioned between CH2Cl2 and H2O
  4. extractionThe organic extract
  5. washwas washed with aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by flash chromatography
  9. washeluting with 50:1 CH2Cl2 /MeOH

Sources & evidence

ORD record
ord-1e3e631e7a94473ca6bb565f0acef7f5
Source dataset
uspto-grants-1997_11
Patent number
US05686455

Reaction notes

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