Sodium Azide → 7-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

HRID 2422484Notes

Reaction equation

HRID 2422484 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>C(O)C>[N:21]([CH2:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[CH:8][C:9](=[O:13])[O:10]2)=[CH:5][CH:4]=1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 597748617-(bromomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

Product 1

HCID 597748747-(azidomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-(bromomethyl)-4-(3-fluorophenyl)-2H-chromen-2-one (1.16 g, 3.5 mmol) in ethanol (35 mL), sodium azide (248 mg, 3.8 mmol) was added. The reaction mixture was then stirred overnight at reflux. After cooling, the reaction mixture was concentrated under reduced pressure and the crude residue was dissolved with CH2Cl2. Salts were removed by filtration and the filtrate was concentrated under reduced pressure to afford the tittle compound. 1H NMR (400 MHz, acetone-d6): 7.72-7.6 (m, 1H), 7.65 (d, 1H), 7.47-7.32 (m, 5H), 6.42 (s, 1H), 4.67 (s, 2H).

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe crude residue was dissolved with CH2Cl2
  5. customSalts were removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto afford the tittle compound

Sources & evidence

ORD record
ord-907345d3cc914918bd586f618760d817
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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