Water → HCID 68280931, compound

HRID 1622856Notes

Reaction equation

HRID 1622856 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].I[CH2:14][CH:15]([CH3:17])[CH3:16].O>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 962WaterHCID 10556Isobutyl iodide2×HCID 24758Sodium hydrideHCID 249055-Bromoindole

Product 1

HCID 68280931HCID 68280931, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 5-bromo-1H-indole (1 g) in DMF (dry) (10 ml) was added NaH (60%, 0.612 g) at room temperature. The mixture was stirred at 80° C. for 10 min. 1-Iodo-2-methylpropane (0.587 mL) was added at room temperature and the mixture was stirred at 80° C. for 1 hr. Another 1-iodo-2-methylpropane (0.587 mL) was added and the mixture was stirred at 80° C. for 1 hr. Water and EtOAc were added and the extracted organic layer was washed with brine. Silica-gel was added to the organic layer and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (silica gel, eluted with EtOAc in hexane) to give the title compound (554 mg) as colorless oil.

Workup

  1. stirringthe mixture was stirred at 80° C. for 1 hr
  2. stirringthe mixture was stirred at 80° C. for 1 hr
  3. washthe extracted organic layer was washed with brine
  4. additionSilica-gel was added to the organic layer
  5. customthe volatiles were removed in vacuo
  6. customwas purified by column chromatography (silica gel, eluted with EtOAc in hexane)

Sources & evidence

ORD record
ord-1bb548703d5a4546814f60c389d96c17
Source dataset
uspto-grants-2014_07
Patent number
US08778934B2

Reaction notes

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