Phosphorus oxybromide → 4-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203077Notes

Reaction equation

HRID 2203077 reaction equation
[CH:1]1([C:4]2[N:8]([CH3:9])[C:7]3[CH:10]=[C:11]([N:14]4[CH:19]=[CH:18][C:17](O)=[CH:16][C:15]4=[O:21])[CH:12]=[CH:13][C:6]=3[N:5]=2)[CH2:3][CH2:2]1.P(Br)(Br)([Br:24])=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:24][C:17]1[CH:18]=[CH:19][N:14]([C:11]2[CH:12]=[CH:13][C:6]3[N:5]=[C:4]([CH:1]4[CH2:3][CH2:2]4)[N:8]([CH3:9])[C:7]=3[CH:10]=2)[C:15](=[O:21])[CH:16]=1

Participants

5

Reactant 3

HCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 896910841-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 896908634-Bromo-1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-oneYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)-4-hydroxypyridin-2(1H)-one (2 g) in DMF (35 ml) was added phosphoryltribromide (2.45 g) at room temperature, and the mixture was stirred at 50° C. overnight. The mixture was poured into saturated NaHCO3 solution, and extracted with EtOAc. The organic layer was washed with water and brine successively, dried over MgSO4 and concentrated in vacua. The resulting residual solid was recrystallized from EtOH-hexane to give the title compound (1.70 g) as a brown solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water and brine successively
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacua
  5. customThe resulting residual solid was recrystallized from EtOH-hexane

Sources & evidence

ORD record
ord-a523cab0eba349daa17ed76968d772c1
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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