Phosphorus oxybromide → 4-Bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinone

HRID 2203007Notes

Reaction equation

HRID 2203007 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15](O)=[CH:14][C:13]4=[O:19])=[CH:8][N:7]3[C:20]=2[CH3:21])[CH2:3][CH2:2]1.P(Br)(Br)([Br:24])=O>CN(C=O)C.CCOC(C)=O.O>[Br:24][C:15]1[CH:16]=[CH:17][N:12]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:20]([CH3:21])=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:5]=3)[CH:8]=2)[C:13](=[O:19])[CH:14]=1

Participants

6

Reactant 2

HCID 24613Phosphorus oxybromideHCID 896902811-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 1213862044-Bromo-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1h)-pyridinone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (3.0 g) in DMF (25 ml) was added phosphorus oxybromide (2.17 ml) at room temperature, and the mixture was stirred at 110° C. for 1 h. The mixture was diluted with EtOAc and water, quenched with saturated NaHCO3 solution, and extracted with EtOAc. The organic layer was separated, washed with water and brine successively, dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (hexane/EtOAc) to give the title compound (0.70 g) as a pale yellow solid.

Workup

  1. customquenched with saturated NaHCO3 solution
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine successively
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-e529529464ca47e2b33a049c12956793
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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