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Phosphorus oxybromide → 4-bromo-1-(2-ethyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497397
Notes
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Reaction equation

HRID 1497397 reaction equation
[CH2:1]([N:3]1[C:11]([CH3:12])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:13]3[CH:18]=[CH:17][C:16](O)=[CH:15][C:14]3=[O:20])=[CH:9]2)=[N:4]1)[CH3:2].P(Br)(Br)([Br:23])=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:23][C:16]1[CH:17]=[CH:18][N:13]([C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[C:11]([CH3:12])[N:3]([CH2:1][CH3:2])[N:4]=3)[CH:9]=2)[C:14](=[O:20])[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 1177986361-(2-ethyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 1177987484-bromo-1-(2-ethyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 51.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(2-ethyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (1.07 g) in N,N-dimethylformamide (20 ml) was added phosphorus oxybromide (1.37 g) at room temperature, and the mixture was stirred at 50° C. overnight. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was recrystallized from ethanol-hexane to give the title compound (680 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-ef280576491a457fa7a1eb89ec9bcaa9
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199963B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes