Phosphorus oxybromide → 4-Bromo-1-(cyclopropylmethyl)pyridin-2(1H)-one

HRID 2276310Notes

Reaction equation

HRID 2276310 reaction equation
P(Br)(Br)([Br:3])=O.[CH:6]1([CH2:9][N:10]2[CH:15]=[CH:14][C:13](O)=[CH:12][C:11]2=[O:17])[CH2:8][CH2:7]1>CN(C=O)C>[Br:3][C:13]1[CH:14]=[CH:15][N:10]([CH2:9][CH:6]2[CH2:8][CH2:7]2)[C:11](=[O:17])[CH:12]=1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 594970981-(Cyclopropylmethyl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 585545154-Bromo-1-(cyclopropylmethyl)pyridin-2(1H)-oneYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Phosphorus oxybromide (5.4 g, 18.9 mmol) was added to a solution of intermediate D2 (1.42 g, 8.6 mmol) in DMF (140 ml) and the mixture was heated at 110° C. for 1 hour. After cooling in an ice bath the solution was partitioned between water and EtOAc. After three extractions with EtOAc, the combined organic fractions were dried (Na2SO4) and the solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D3 (1.82 g, 93%).

Workup

  1. temperatureAfter cooling in an ice bath the solution
  2. customwas partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc
  4. dry with materialthe combined organic fractions were dried (Na2SO4)
  5. customthe solvent was evaporated in vacuo
  6. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  7. customThe desired fractions were collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-21007687803c43c7862e90e9a341f5fd
Source dataset
uspto-grants-2015_09
Patent number
US09132122B2

Reaction notes

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