Sodium Azide → HCID 85939649, compound

HRID 2118350Notes

Reaction equation

HRID 2118350 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([F:19])[CH:6]=1)=[O:4].[N-:20]=[N+:21]=[N-:22].[Na+]>CN(C=O)C>[N:20]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([F:19])[CH:6]=1)=[O:4])=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 19862694HCID 19862694, compound

Product 1

HCID 85939649HCID 85939649, compoundYield 91.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-bromo-1-[4-(benzyloxy)-3-fluorophenyl]ethanone (J. Med. Chem. 1980, 23, 738-744) (1 g) in dry DMF (2.5 mL) was cooled to 150 and treated portionwise with sodium azide (220 mg). After complete addition the reaction mixture was stirred for a further 1 h. The reaction mixture was partitioned between EtOAc and water. The organic phase was washed with water and the combined aqueous phase back extracted with EtOAc. The combined organic phases were washed with sat. NaHCO3(aq) three times and the combined washes back extracted with EtOAc. The combined organic phase was washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography on silica, eluting with hexane-EtOAc (4:1 and 2:1) to give the title compound (810 mg). LCMS RT=3.61 min.

Workup

  1. additionAfter complete addition the reaction mixture
  2. customThe reaction mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with water
  4. extractionthe combined aqueous phase back extracted with EtOAc
  5. washThe combined organic phases were washed with sat. NaHCO3(aq) three times
  6. extractionthe combined washes back extracted with EtOAc
  7. washThe combined organic phase was washed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography on silica
  11. washeluting with hexane-EtOAc (4:1 and 2:1)

Sources & evidence

ORD record
ord-2a7a1ce4836d41d7ab19ba803219bbde
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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