Pyridine → 4-(tert-Butyldimethylsilyloxymethyl)-1-(3,4,5-trimethoxyphenyl)imidazole

HRID 993033Notes

Reaction equation

HRID 993033 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Si:16]([O:23][CH2:24][C:25]1[N:26]=[CH:27][NH:28][CH:29]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].N1C=CC=CC=1>ClCCl.C(O[Cu]OC(=O)C)(=O)C>[Si:16]([O:23][CH2:24][C:25]1[N:26]=[CH:27][N:28]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[CH:29]=1)([C:19]([CH3:22])([CH3:20])[CH3:21])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 178455170HCID 178455170, compound

Product 1

HCID 184085384-(tert-Butyldimethylsilyloxymethyl)-1-(3,4,5-trimethoxyphenyl)imidazole

Reagents, catalysts & solvents 2

HCID 178476681HCID 178476681, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3,4,5-Trimethoxyphenylboronic acid (1.56 g) and 4-(tert-butyldimethylsilyloxymethyl)imidazole (1.26 g) were dissolved in dichloromethane (10 mL), and to the solution pyridine (562 mg) was added. Bisacetoxycopper (1.29 g) was then added to the mixture, and the mixture was stirred overnight at room temperature under an argon atmosphere. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=50:1) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-a4f82d4826da4af3bac4a796656eee5b
Source dataset
uspto-grants-2002_10
Patent number
US06472386B1

Reaction notes

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