Water → 2-(4-Bromophenoxy)-3-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridine

HRID 573336Notes

Reaction equation

HRID 573336 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][O:12][CH2:13][CH2:14][N:15]1[C:19]2=[N:20][CH:21]=[CH:22][CH:23]=[C:18]2[N:17]=[C:16]1S(C)(=O)=O.O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:16]2[N:15]([CH2:14][CH2:13][O:12][CH3:11])[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[N:17]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78084-BromophenolHCID 24758Sodium hydrideHCID 667277733-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 667277232-(4-Bromophenoxy)-3-(2-methoxyethyl)-3H-imidazo[4,5-b]pyridineYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-bromophenol (149 mg) in DMF (4 mL) was added NaH (60% in oil, 36.0 mg) at room temperature. The mixture was stirred at room temperature for 30 min. To the mixture was added 3-(2-methoxyethyl)-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (200 mg). The mixture was exposed to microwave irradiation at 180° C. for 30 min, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (243 mg).

Workup

  1. customirradiation at 180° C. for 30 min
  2. extractionextracted with AcOEt
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-57e5f84173374060a9f1e83bfca54484
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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