Sodium Azide → HCID 12018138, compound

HRID 1017568Notes

Reaction equation

HRID 1017568 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:28])[O:13][C:14](=[O:27])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25]Cl)[CH:17]=2)=[CH:3]1.[N-:29]=[N+:30]=[N-:31].[Na+]>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:28])[O:13][C:14](=[O:27])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][CH2:24][CH2:25][N:29]=[N+:30]=[N-:31])[CH:17]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 12018137HCID 12018137, compound

Product 1

HCID 12018138HCID 12018138, compoundYield 113%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 3-(1-methylindol-3-yl)-4-[3-(3-chloropropyloxy)phenyl]furan-2,5-dione (1.0 g, 2.2 mmol) in DMF (15 mL) was added sodium azide (0.43 g, 3 eq.) and the resulting mixture was heated at 75° C. for 24 h. The reaction mixture was cooled to room temperature and quenched with water. The product was then extracted into EtOAc. The EtOAc layer was washed with H2O, NaCl (sat.), dried over Na2SO4, and concentrated in vacuo to give 3-(1-methylindol-3-yl)-4-[3-(3-azidopropyloxy)phenyl]furan-2,5-dione (1.0 g) which was used directly in the next step without any further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with water
  3. extractionThe product was then extracted into EtOAc
  4. washThe EtOAc layer was washed with H2O, NaCl (sat.)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec5f74330c694462b0c04d6009333828
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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