Isopropyl iodide → HCID 22732008, compound

HRID 2084056Notes

Reaction equation

HRID 2084056 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[H-].[Na+].I[CH:20]([CH3:22])[CH3:21]>C1(C)C=CC=CC=1.O.CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][N:8]2[CH:20]([CH3:22])[CH3:21])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 6764936-Bromoindole

Product 1

HCID 22732008HCID 22732008, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-bromoindole (2.0 g, 10 mmol), K2CO3 (2.76 g, 20 mmol), NaH (0.48 g, 20 mmol), DMF (1 ml) and 2-iodopropane (8.5 g, 50 mmol) in 40 ml of toluene was heated at 90˜100° C. for 2 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate (Na2SO4), concentrated in vacuo and the residue purified by column chromatography on silica gel, eluting with hexanes, to give (2.32 g, 97%) of the title product.

Workup

  1. temperaturewas heated at 90˜100° C. for 2 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with hexanes

Sources & evidence

ORD record
ord-8ef3b2b1d8a54147a0783d9b8c5da062
Source dataset
uspto-grants-2004_04
Patent number
US06716837B1

Reaction notes

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