Imidazole → HCID 17946394, compound

HRID 493345Notes

Reaction equation

HRID 493345 reaction equation
[CH3:1][Si:2](Cl)([CH3:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[Br:9][C:10]1[C:15]([O:16][CH2:17][CH2:18][OH:19])=[CH:14][CH:13]=[CH:12][N:11]=1.N1C=CN=C1>CN(C=O)C.[OH-].[Na+]>[Br:9][C:10]1[C:15]([O:16][CH2:17][CH2:18][O:19][Si:2]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:7])[CH3:1])=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 220362632-[(2-Bromopyridin-3-yl)oxy]ethan-1-ol

Product 1

HCID 17946394HCID 17946394, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A solution of dimethyl-t-butylsilyl chloride (11.1 g, 74 mmol) in DMF (30 mL) was added to a suspension of 2-bromo-3-(2-hydroxyethoxy)pyridine (15.3 g, 70 mmol; obtained in Example 191, Step 1) and imidazole (10.0 g, 147 mmol) in DMF (30 mL). The reaction mixture was stirred at ambient temperature for 2 h, diluted with 0.5 M aqueous NaOH (0.7 L), and extracted twice with toluene. The combined organic phases were washed once with water, dried (MgSO4), and concentrated. The resulting oil was treated with a mixture of petroleum ether and ethyl acetate (95:5; 50 mL) and an analytical sample of white crystals was collected. The remaining crystals were mixed with the filtrate, the solvent was evaporated and the resulting crude product was used directly in the next step. Solid; yield 18.3 g (78%); mp 81° C. Anal. (C13H22BrNO2Si) C, H, N.

Workup

  1. extractionextracted twice with toluene
  2. washThe combined organic phases were washed once with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionThe resulting oil was treated with a mixture of petroleum ether and ethyl acetate (95:5; 50 mL)
  6. customan analytical sample of white crystals was collected
  7. additionThe remaining crystals were mixed with the filtrate
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-68c97729837e420bb6cc6b23c9b44e91
Source dataset
uspto-grants-2009_05
Patent number
US07534794B2

Reaction notes

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