Phosphorus oxychloride → 4-(2-Benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole

HRID 1445763Notes

Reaction equation

HRID 1445763 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([NH:15][C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=1[F:24])[C:12](=O)[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[N:15]=[C:16]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:18]=2[F:24])[O:25][C:12]=1[CH3:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58951463N-[1-(2-Benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide2×

Product 1

HCID 589514114-(2-Benzyloxy-ethyl)-2-(4-bromo-2-fluoro-phenyl)-5-methyl-oxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of N-[1-(2-benzyloxy-ethyl)-2-oxo-propyl]-4-bromo-2-fluoro-benzamide (1.0 mmol) (See Intermediate 36) in dimethylformamide (0.25M), slowly add phosphorus oxychloride (3.0 mmol) and heat to 90° C. for 2.5 hours. After this time, remove the heat and carefully add water (same amount as DMF) and allow the reaction to cool to room temperature before extracting with ether. Wash organics with water and brine. Dry the organics with sodium sulfate, filter and concentrate in vacuo. Purify via radial chromatography eluting with ethyl acetate and hexane. MS (m/e) (79Br/81Br): 390.2/392.2 (M+1)

Workup

  1. customAfter this time, remove the
  2. temperatureheat
  3. customthe reaction
  4. extractionbefore extracting with ether
  5. dry with materialDry the organics with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify via radial chromatography
  9. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-65ef94116c9449c6bca22a5257c7de1b
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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