Acetone → HCID 58754814, compound

HRID 1711238Notes

Reaction equation

HRID 1711238 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH:13]=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=2)[CH:3]=1.C([Mg]Cl)(C)C.C([Li])CCC.[CH3:42][C:43]([CH3:45])=[O:44].[NH4+].[Cl-]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:24])([CH3:25])[CH3:23])[C:13]([C:43]([OH:44])([CH3:45])[CH3:42])=[C:14]([C:16]#[N:17])[N:15]=2)=[O:10])=[C:4]([C:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=2)[CH:3]=1

Participants

8

Reactant 5

HCID 180AcetoneHCID 25517Ammonium ChlorideHCID 594575324-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-bromo-2-cyclohex-1-enyl-phenyl)-amideHCID 178418339ButyllithiumHCID 178418918HCID 178418918, compound

Product 1

HCID 58754814HCID 58754814, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4-bromo-2-cyclohex-1-enyl-phenyl)-amide (as prepared in Example 11, step (f), 50.0 mg, 0.100 mmol) in 1 mL of THF at −78° C. under Ar was added isopropyl magnesium chloride (55 μL, 0.11 mmol, 2.0 M in THF). The resulting mixture was warmed to RT and stirred for 15 min, cooled back to −78° C. To the mixture was added n-butyllithium (55 μL, 0.11 mmol, 2.0 M in cyclohexane) and the resulting mixture was stirred at −78° C. for 0.5 h under Ar. Acetone (30 μL, 0.40 mmol) was added and the reaction was warmed to RT and stirred for 16 h under Ar. Treated with 5 mL of saturated NH4Cl aqueous solution followed by 30 mL of EtOAc, the mixture was washed with H2O (10 mL), brine (5 mL) and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (5-10% EtOAc/hexane) to afford 40.0 mg (84%) of the title compound as a white solid. Mass spectrum (ESI, m/z): Calcd. for C26H35BrN4O3Si, 559.2 (M+H), found 558.9.

Workup

  1. temperaturecooled back to −78° C
  2. stirringthe resulting mixture was stirred at −78° C. for 0.5 h under Ar
  3. temperaturethe reaction was warmed to RT
  4. stirringstirred for 16 h under Ar
  5. washthe mixture was washed with H2O (10 mL), brine (5 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by flash chromatography on silica gel (5-10% EtOAc/hexane)

Sources & evidence

ORD record
ord-3c0c94ce80e7410ebcca88e862e72477
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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