Imidazole → HCID 632411, compound

HRID 1069520Notes

Reaction equation

HRID 1069520 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([I:12])[C:9]([OH:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].N1C=CN=C1>CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]([I:12])[C:9]([O:13][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 2788ClioquinolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 632411HCID 632411, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A flame-dried, 50-mL, three-necked flask is charged with 5-chloro-8-hydroxy-7-iodoquinoline (2.814 g), which is commercially available, t-butyldimethylchlorosilane (1.76 g), and 10 mL of DMF. Imidazole (1.66 g) is added, and the resulting mixture is stirred at room temperature for 18 h. The reaction mixture is then quenched with 10 mL of saturated aqueous NaHCO3 and extracted with hexane three times. The combined organic layers are dried over MgSO4, filtered and concentrated to give 3.898 g of the title compound as a pale green solid.

Workup

  1. customThe reaction mixture is then quenched with 10 mL of saturated aqueous NaHCO3
  2. extractionextracted with hexane three times
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-29981cf1cb67451b838cfbf45d392d87
Source dataset
uspto-grants-2001_06
Patent number
US06252080B1

Reaction notes

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