Water → 5-Fluoro-1-(2-oxiranylmethyl)-1H-indole

HRID 1532616Notes

Reaction equation

HRID 1532616 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.[F:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.[H-].[Na+].O>CN(C=O)C>[CH2:1]([N:12]1[C:13]2[C:9](=[CH:8][C:7]([F:6])=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)[CH:3]1[O:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 678615-Fluoroindole

Product 1

HCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indoleYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Epibromohydrin (1.4 ml, 16.5 mmole) was added to a stirred solution of 5-fluoroindole (2.0 g, 15 mmole) and sodium hydride (0.66 g, 16.5 mmole) in anhydrous DMF (20 ml), and the mixture was heated at 60° C. under nitrogen for 15 hours. Water (100 ml) was added and the product extracted into CH2Cl2 (3×35 ml). The combined organics were washed with water (25 ml), brine (25 ml) and dried over anhydrous sodium sulfate. Filtration and concentration in vacuo gave the crude product as a viscous yellow colored oil (2.7 g). This was purified by flash silica gel chromatography (30% ethyl acetate in hexane) to afford the titled product as a viscous oil (2.5 g, 89% yield).

Workup

  1. extractionthe product extracted into CH2Cl2 (3×35 ml)
  2. washThe combined organics were washed with water (25 ml), brine (25 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationFiltration and concentration in vacuo
  5. customgave the crude product as a viscous yellow colored oil (2.7 g)
  6. customThis was purified by flash silica gel chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-3b2fc20ab0e0475988855526f8b22525
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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