Phosphorus oxybromide → HCID 59497109, compound

HRID 2276323Notes

Reaction equation

HRID 2276323 reaction equation
P(Br)(Br)([Br:3])=O.[CH:6]1([C:9]2[C:10](=[O:20])[N:11]([CH2:16][CH:17]3[CH2:19][CH2:18]3)[CH:12]=[CH:13][C:14]=2O)[CH2:8][CH2:7]1>CN(C=O)C>[Br:3][C:14]1[CH:13]=[CH:12][N:11]([CH2:16][CH:17]2[CH2:19][CH2:18]2)[C:10](=[O:20])[C:9]=1[CH:6]1[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 59497083HCID 59497083, compound

Product 1

HCID 59497109HCID 59497109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Phosphorus oxybromide (2.4 g, 8.28 mmol) was added to a solution of intermediate D35 (0.85 g, 4.14 mmol) in DMF (60 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. The mixture was extracted with EtOAc (3×200 ml), 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 D36 (0.99 g, 89%).

Workup

  1. temperatureAfter cooling in an ice bath
  2. customthe solution was partitioned between water and EtOAc
  3. extractionThe mixture was extracted with EtOAc (3×200 ml)
  4. dry with materialthe combined organic fractions were 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
  9. customto yield intermediate D36 (0.99 g, 89%)

Sources & evidence

ORD record
ord-36bb5cedd2d24cceb1623e321592d350
Source dataset
uspto-grants-2015_09
Patent number
US09132122B2

Reaction notes

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