Sodium hydride → HCID 66727797, compound

HRID 573362Notes

Reaction equation

HRID 573362 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1S(C)(=O)=O.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([F:23])[CH:17]=1.[H-].[Na+]>>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:3]2[N:2]([CH3:1])[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:5]3[N:4]=2)=[C:18]([F:23])[CH:17]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 27249814-Bromo-2-fluorophenolHCID 585773713-Methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine

Product 1

HCID 66727797HCID 66727797, compound

Conditions

Temperature
180 °C

Procedure

A suspension of 3-methyl-2-(methylsulfonyl)-3H-imidazo[4,5-b]pyridine (700 mg), 4-bromo-2-fluorophenol (0.399 mL) and NaH (60% in oil, 159 mg) was heated at 180° C. for 30 min under microwave irradiation. The mixture was quenched with water at room temperature and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (691 mg).

Workup

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with AcOEt
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-e8a282c607034775b77a0337e8a9ec79
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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