4-Bromophenol → 2-(4-Bromophenoxy)imidazo[1,2-a]pyridine

HRID 573278Notes

Reaction equation

HRID 573278 reaction equation
Cl[C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]2[C:10]=1C(OCC)=O.[CH:16]1[C:21]([OH:22])=[CH:20][CH:19]=[C:18]([Br:23])[CH:17]=1.[H-].[Na+].[Cl-].[Cl-].[Ca+2]>CN(C=O)C.CO>[Br:23][C:18]1[CH:19]=[CH:20][C:21]([O:22][C:2]2[N:3]=[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][N:5]3[CH:10]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 78084-BromophenolHCID 24758Sodium hydrideHCID 5284359Calcium ChlorideHCID 21643308Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate

Product 1

HCID 679931672-(4-Bromophenoxy)imidazo[1,2-a]pyridineYield 20.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (2.00 g) was added to a solution of p-bromophenol (1.617 g) and NaH (0.427 g) in DMF (10 mL) at 100° C. The mixture was stirred at 100° C. under a dry atmosphere (CaCl2 tube) overnight. The reaction mixture was diluted with MeOH, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (530 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-a303b031cdc644cb8d1c3fc4e8821dcd
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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