Phosphorus oxybromide → HCID 59497086, compound

HRID 404700Notes

Reaction equation

HRID 404700 reaction equation
P(Br)(Br)([Br:3])=O.[CH:6]1([CH2:9][N:10]2[CH:15]=[CH:14][C:13](O)=[C:12]([C:17]([F:20])([F:19])[F:18])[C:11]2=[O:21])[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:21])[C:12]=1[C:17]([F:20])([F:19])[F:18]

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 59497082HCID 59497082, compound

Product 1

HCID 59497086HCID 59497086, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Phosphorus oxybromide (7.03 g, 24.5 mmol) was added to a solution of intermediate D8 (2.60 g, 11.1 mmol) in DMF (50 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 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 D9 (1.38 g, 42%).

Workup

  1. temperatureAfter cooling in 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. customthe solvent 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-562dc832deeb489495c7c4fc466fbe56
Source dataset
uspto-grants-2014_06
Patent number
US08748621B2

Reaction notes

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