Water → 3-(3-azidopropyl)-5-fluoro-1H-indole

HRID 1835120Notes

Reaction equation

HRID 1835120 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[NH:7][CH:6]=1.[N-:15]=[N+:16]=[N-:17].[Na+].O>CN(C)C=O>[N:15]([CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)[NH:7][CH:6]=1)=[N+:16]=[N-:17]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 114026013-(3-bromopropyl)-5-fluoro-1H-indole

Product 1

HCID 113449903-(3-azidopropyl)-5-fluoro-1H-indoleYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(3-bromopropyl)-5-flouro-1H-indole (0.95 g, 3 mmol) and sodium azide (0.59 g, 9 mmol) in anhydrous dimethyl formamide is stirred at 60° C. for 18 h, poured into water and extracted with methylene chloride. The extracts are combined, washed with water, dried over Na2SO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7) to afford the title product as a clear oil, 0.98 g (91% yield), identified by NMR and mass spectral analyses.

Workup

  1. extractionextracted with methylene chloride
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue is purified by flash chromatography (silica gel, EtOAc/hexane: 3/7)

Sources & evidence

ORD record
ord-d58266908257492e9eaef2e6c6686d3f
Source dataset
uspto-grants-2004_08
Patent number
US06770642B2

Reaction notes

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