Water → HCID 15524201, compound

HRID 1532617Notes

Reaction equation

HRID 1532617 reaction equation
[CH2:1]([CH:3]1[O:5][CH2:4]1)Br.[CH3:6][O:7][C:8]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[CH:11][NH:12]2.[H-].[Na+].O>CN(C=O)C>[CH2:1]([N:12]1[C:13]2[C:9](=[C:8]([O:7][CH3:6])[CH:16]=[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 1383634-Methoxy-1H-indole

Product 1

HCID 15524201HCID 15524201, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Epibromohydrin (0.64 ml, 7.5 mmole) was added to a stirred solution of 4-methoxyindole (1.0 g, 6.8 mmole) and sodium hydride (0.3 g, 7.8 mmole) in anhydrous DMF (20 ml), and the mixture was heated at 60° C. under nitrogen for two hours. Water (100 ml) was added and the product extracted into CH2Cl2 (3×25 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 yellow colored oil (1.5 g). This was purified by flash silica gel chromatography (30% ethyl acetate in hexane) to afford the titled product as a light oil (1.27 g, 92% yield).

Workup

  1. extractionthe product extracted into CH2Cl2 (3×25 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 yellow colored oil (1.5 g)
  6. customThis was purified by flash silica gel chromatography (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-463dc1e033c24e6894392913ea749f60
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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