Imidazole → HCID 67414669, compound

HRID 906041Notes

Reaction equation

HRID 906041 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][Si:27]([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2838541HCID 2838541, compound

Product 1

HCID 67414669HCID 67414669, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-N-(4-hydroxyphenyl)benzamide in DMF (1.3 M), 2.5 eq of imidazole and 1.2 eq of TBDMSCl were added and the solution stirred at RT for 30 minutes. The reaction mixture was diluted with EtOAc. The organic phase was washed with aqueous HCl (1N), saturated aqueous NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (95%); MS (ES+) m/z 406 (M+H)+, m/z 408 (M+H)+

Workup

  1. washThe organic phase was washed with aqueous HCl (1N), saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ffe561488a664e7d9e7bd20169b639c6
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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