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

HRID 2362802Notes

Reaction equation

HRID 2362802 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 on an ice bath the solution was partitioned between water and EtOAc. After three extractions with EtOAc the combined organic fractions were dried (Na2SO4), filtered 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 on an ice bath the solution
  2. customwas partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc the combined organic fractions
  4. dry with materialwere dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d889dbd4d5ba47fd9d1939007d57e1a5
Source dataset
uspto-grants-2014_04
Patent number
US08691849B2

Reaction notes

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