Water → 5-Fluoro-indolyl-3-propylazide

HRID 1596770Notes

Reaction equation

HRID 1596770 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11](Br)[CH2:12][CH3:13])=[CH:5]2.[N-:15]=[N+:16]=[N-:17].[Na+].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11]([N:15]=[N+:16]=[N-:17])[CH2:12][CH3:13])=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 540585145-Fluoro-indolyl-3-propylbromide

Product 1

HCID 543589695-Fluoro-indolyl-3-propylazideYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 5-fluoro-indolyl-3-propylbromide (10.67 g, 41 mmol) and sodium azide (3.9 g, 60 mmol) in anhydrous N,N-dimethylformamide (60 ml) was allowed to stir at 60° C. for 18 hours. The mixture was poured into water (150 ml), extracted with methylene chloride (3×150 ml), washed with water (3×100 ml). The organic layer was dried over sodium sulfate, filtered and the solvent was removed under vacuurml Chromatography (30% ethyl acetate-hexanes) afforded 8.10 g (89%) of product as a clear oil.

Workup

  1. extractionextracted with methylene chloride (3×150 ml)
  2. washwashed with water (3×100 ml)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed under vacuurml Chromatography (30% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-be9c644df7e24c18b110d4ed12919788
Source dataset
uspto-grants-2001_09
Patent number
US06291683B1

Reaction notes

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