1-Methylimidazole → HCID 10117835, compound

HRID 346987Notes

Reaction equation

HRID 346987 reaction equation
[Li]CCCC.[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:22]=[C:23]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([C:37](=[O:47])[C:38]4[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=4)[CH:35]=3)[N:30]([CH3:48])[C:29](=[O:49])[CH:28]=2)[CH:24]=[CH:25][CH:26]=1>C1COCC1.O>[Cl:20][C:21]1[CH:22]=[C:23]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([C:37]([OH:47])([C:11]4[N:7]([CH3:6])[CH:8]=[N:9][CH:10]=4)[C:38]4[CH:43]=[CH:42][C:41]([N+:44]([O-:46])=[O:45])=[CH:40][CH:39]=4)[CH:35]=3)[N:30]([CH3:48])[C:29](=[O:49])[CH:28]=2)[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 13819ChlorotriethylsilaneHCID 21082023HCID 21082023, compoundHCID 178418339Butyllithium2×

Product 1

HCID 10117835HCID 10117835, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n BuLi (1.6M in hexane) (4.4 ml, 0.0071 mol) was added dropwise at −70° C. to a solution of 1-methyl-1H-imidazole (0.0071 mol) in THF (8 ml) under N2 flow. The mixture was stirred for 15 minutes. ClSiEt3 (0.0073 mol) was added dropwise at −70° C. The mixture was stirred for 15 minutes. BuLi (1.6M in hexane) (3.9 ml, 0.0062 mol) was added dropwise at −70° C. The mixture was stirred at −70° C. for 15 minutes. A solution of 4-(3-chlorophenyl)-1-methyl-6-(4-nitrobenzoyl)-2(1H)-quinolinone (described in Example A3d) (0.0040 mol) in THF (15 ml) was added. The mixture was stirred at −70° C. for 15 minutes, poured out into H2O and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from diethyl ether. The precipitate was filtered off and dried, yielding 0.54 g (27%) of (±)-4-(3-chlorophenyl)-6-[hydroxy(1-methyl-1H-imidazol-5-yl)(4-nitrophenyl)methyl]-1-methyl-2(1H)-quinolinone, mp. 230° C.

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. stirringThe mixture was stirred at −70° C. for 15 minutes
  3. stirringThe mixture was stirred at −70° C. for 15 minutes
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 95/5/0.2; 15–40 μm)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customThe residue was crystallized from diethyl ether
  13. filtrationThe precipitate was filtered off
  14. customdried

Sources & evidence

ORD record
ord-d5a484fc920940c5a724f675e27a696b
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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