Imidazole → HCID 67377025, compound

HRID 1023355Notes

Reaction equation

HRID 1023355 reaction equation
[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][C:7]2[N:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)=[C:4]([Cl:17])[CH:3]=1.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25].C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:15]=[C:14]([CH3:16])[C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([O:13][Si:27]([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28])=[CH:11][N:12]=2)=[C:4]([Cl:17])[CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 67327021HCID 67327021, compound

Product 1

HCID 67377025HCID 67377025, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF (50 mL) solution of 6-(4-bromo-2-chloro-6-methylphenoxy)pyridin-3-ol (5.00 g) were added imidazole (1.41 g) and TBDMSCl (2.87 g) at room temperature. After stirring at room temperature for 5 hours, to the reaction mixture was added saturated aqueous NaHCO3, and extracted with AcOEt. The organic layer was washed with water, saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 2/1) to give 2-(4-bromo-2-chloro-6-methylphenoxy)-5-{[tert-butyl(dimethyl)silyl]oxy}pyridine as a colorless oil (6.16 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water, saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=9/1 to 2/1)

Sources & evidence

ORD record
ord-e0e5d59484ee40dcb3c36aef3b33f4ef
Source dataset
uspto-grants-2014_05
Patent number
US08722663B2

Reaction notes

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