Imidazole → HCID 17985854, compound

HRID 910122Notes

Reaction equation

HRID 910122 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[CH:18]([OH:20])[CH3:19])[CH:11]=[CH:10]1.N1C=CN=C1>O1CCCC1>[Si:1]([O:20][CH:18]([C:16]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:17]=1[NH:9][CH:10]=[CH:11]2)[CH3:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 17985621HCID 17985621, compound

Product 1

HCID 17985854HCID 17985854, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Add tert-butyldimethylsilyl chloride (16.4 g, 108 mmol) in anhydrous tetrahydrofuran (100 ml) to 1-(indol-7-yl)ethan-1-ol (10.7 g, 66.4 mmol) and imidazole (11.8 g, 173 mmol) in anhydrous tetrahydrofuran (100 ml). Stir at 20° C. for 2 hours. Dilute with hexanes (400 ml). Wash with 0.25 M aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. Dry over magnesium sulfate and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with hexane containing 10-25% ethyl acetate to provide the desired compound (16 g, 87%) as a colorless oil.

Workup

  1. washWash with 0.25 M aqueous sodium bicarbonate
  2. dry with materialDry over magnesium sulfate
  3. concentrationconcentrate under reduced pressure
  4. washeluting with hexane containing 10-25% ethyl acetate

Sources & evidence

ORD record
ord-d5a3827b05a14d3d9f523043b6690e15
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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