Imidazole → HCID 20077469, compound

HRID 1655026Notes

Reaction equation

HRID 1655026 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1>CN(C=O)C.C([O-])(O)=O.[Na+]>[O:1]([C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 135689357HCID 135689357, compound

Product 1

HCID 20077469HCID 20077469, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 7-hydroxy-4-phenylquinoline (366 mg), tert-butyldimethylsilyl chloride (200 mg) and imidazole (282 mg) in DMF (2 mL) was stirred at r.t. for 17 hr and then diluted with 5% aq. NaHCO3 (20 mL). The mixture was extracted with EtOAc (3×) and the combined organics were washed with H2O (3×), brine, dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel; EtOAc/hexane (15:85)) provided the title compound as a solid.

Workup

  1. extractionThe mixture was extracted with EtOAc (3×)
  2. washthe combined organics were washed with H2O (3×), brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6f308ac6f6424451a34ca337bf79d42d
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

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