Imidazole → HCID 68453232, compound

HRID 1479930Notes

Reaction equation

HRID 1479930 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([I:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl>[Si:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]([I:12])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 961115-Iodo-8-quinolinol

Product 1

HCID 68453232HCID 68453232, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

8-Hydroxy-5-iodoquinoline (7.0 g, 25.8 mmol), imidazole (1.85 g, 27.2 mmol) and tert-butyldimethylsilyl chloride (4.28 g, 28.4 mmol) are dissolved in anhydrous CH2Cl2 (40 ml) under N2. The mixture is stirred vigorously overnight, then diluted with CH2Cl2 (60 ml) and washed with 5% aqueous HCl (2×30 ml) and water (40 ml). The organic phase is dried over sodium sulfate, and the solvent is distilled off under reduced pressure, leaving a brown liquid. This crude product is purified by flash chromatography on silica (heptane:ethyl acetate 5:1). The end product is isolated as pale-yellow solid (8 g, 80%).

Workup

  1. washwashed with 5% aqueous HCl (2×30 ml) and water (40 ml)
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customleaving a brown liquid
  5. customThis crude product is purified by flash chromatography on silica (heptane:ethyl acetate 5:1)

Sources & evidence

ORD record
ord-ef1368c8e3464ea6b05b10c1d4b12eeb
Source dataset
uspto-grants-2016_08
Patent number
US09409883B2

Reaction notes

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