Imidazole → 3-Bromo-6-(tert-butyldimethylsilyloxy)picolinonitrile

HRID 340198Notes

Reaction equation

HRID 340198 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](=[O:8])[NH:4][C:3]=1[C:9]#[N:10].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C=O)C.O>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([O:8][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 668751023-Bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile

Product 1

HCID 668757543-Bromo-6-(tert-butyldimethylsilyloxy)picolinonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 3-bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile (from step 2) (1.0 eq.), tert-butyldimethylsilylchloride (TBSCl) (1.8 eq.), and imidazole (2.5 eq.) in DMF (0.2 M) was heated to 60° C. and stirred overnight. The reaction mixture was diluted with water and extracted with ether. The combined organic layers were dried over anhydrous MgSO4 and concentrated en vacuo. The residue was purified by a COMBIFLASH® system (ISCO) using 0-20% ethyl acetate in hexane to give 3-bromo-6-(tert-butyldimethylsilyloxy)picolinonitrile.

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  3. concentrationconcentrated en vacuo
  4. customThe residue was purified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-fadf6516f71b42049b6a7442dd297b70
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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