Imidazole → HCID 57706957, compound

HRID 1662387Notes

Reaction equation

HRID 1662387 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6]([C:7]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:22]=[C:21]([OH:23])[CH:20]=[CH:19][C:18]=2[F:24])=[CH:5][CH2:4][CH2:3]1.N1C=CN=C1.[CH:31]([Si:34](Cl)([CH:38]([CH3:40])[CH3:39])[CH:35]([CH3:37])[CH3:36])([CH3:33])[CH3:32]>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1([CH3:25])[C:6]([C:7]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][C:8]=2[C:17]2[CH:22]=[C:21]([O:23][Si:34]([CH:38]([CH3:40])[CH3:39])([CH:35]([CH3:37])[CH3:36])[CH:31]([CH3:33])[CH3:32])[CH:20]=[CH:19][C:18]=2[F:24])=[CH:5][CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 57706368HCID 57706368, compound

Product 1

HCID 57706957HCID 57706957, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 66.14B (77.0 mg, 226 μmol) in DMF (10 mL) was added imidazole (30.8 mg, 452 μmol) and then triisopropylsilyl chloride (58.1 μL, 271 μmol). The resulting mixture was then stirred for 4 hours. The reaction was diluted with EtOAc and washed with 1N HCl, water, and brine. The organic phase was dried over sodium sulfate, filtered, concentrated, and purified by silica gel chromatography (0 to 10% EtOAc/Hexanes) to provide 66.14C (90.0 mg, 80.1% yield).

Workup

  1. washwashed with 1N HCl, water, and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0 to 10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-3c7790ff5a024c18b048e345aab37056
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

Loading…