Imidazole → HCID 22556728, compound

HRID 983936Notes

Reaction equation

HRID 983936 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2.N1C=CN=C1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>CN(C)C=O>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 22556873HCID 22556873, compound

Product 1

HCID 22556728HCID 22556728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2-hydroxyethyl)indole (2.86 g, 17.7 mmol) in 25 mL of dry dimethylformamide was added imidazole (2.54 g, 37.3 mmol) followed by triisopropylsilyl chloride (4.35 mL, 19.7 mmol) and the mixture stirred at room temperature under nitrogen for 3 hours. After diluting with hexanes (500 mL) the organic layer was washed with water (2×50 mL) and saturated aqueous sodium chloride (1×50 mL) and dried over magnesium sulfate. The mixture was filtered and concentrated under reduced pressure to provide 7-(2-(triisopropylsilyloxy)eth-1-yl)indole. This indole was reacted essentially as described in Preparation II to provide the title compound as a yellow solid.

Workup

  1. washwas washed with water (2×50 mL) and saturated aqueous sodium chloride (1×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe mixture was filtered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a0e2fa8cd53a4e03a3b88f469e588263
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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