1-Methylimidazole → HCID 9804515, compound

HRID 895150Notes

Reaction equation

HRID 895150 reaction equation
C([Li])CCC.[CH3:6][N:7]1[CH:11]=[CH:10][N:9]=[CH:8]1.Cl[Si](CC)(CC)CC.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]2[CH:39]=[CH:40][N:41]=[C:34]2[CH:33]=[C:32]3[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[O:28])=[CH:23][CH:22]=1>C1COCC1.O>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([C:11]2[N:7]([CH3:6])[CH:8]=[N:9][CH:10]=2)([C:29]2[CH:30]=[C:31]3[C:36](=[CH:37][CH:38]=2)[N:35]2[CH:39]=[CH:40][N:41]=[C:34]2[CH:33]=[C:32]3[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[OH:28])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 13819ChlorotriethylsilaneHCID 22385771HCID 22385771, compoundHCID 178418339Butyllithium2×

Product 1

HCID 9804515HCID 9804515, compoundYield 18.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (0.0129 mol) was added slowly at −70° C. under N2 flow to a solution of 1-methylimidazole (0.0129 mol) in THF (25 ml). The mixture was stirred for 30 min. Chlorotriethylsilane (0.0129 mol) was added. The mixture was allowed to warm to room temperature and then cooled to −70° C. n-Butyllithium (0.0129 mol) was added. The mixture was stirred at −70° C. for 1 hour, then allowed to warm to −15° C. and cooled to −70° C. A solution of (±)-α-(4-chlorophenyl)-5-phenylimidazo[1,2-a]quinoline-7-methanone (0.0107 mol) in THF (12 ml) was added. The mixture was stirred at −70° C. for 1 hour. Water was added The mixture was extracted with EtOAc. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel. The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 0.9 g (18%) of (±)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-5-phenylimidazo[1,2-a]quinoline-7-methanol (compound 11).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at −70° C. for 1 hour
  3. temperatureto warm to −15° C.
  4. temperaturecooled to −70° C
  5. stirringThe mixture was stirred at −70° C. for 1 hour
  6. extractionwas extracted with EtOAc
  7. customThe organic layer was separated
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was purified by column chromatography over silica gel
  12. customThe pure fractions were collected
  13. customthe solvent was evaporated
  14. customThe residue was crystallized from 2-propanone
  15. filtrationThe precipitate was filtered off
  16. customdried

Sources & evidence

ORD record
ord-e0f351ac399b4e96b289241f172a54e4
Source dataset
uspto-grants-2005_07
Patent number
US06914066B2

Reaction notes

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