Allyl bromide → HCID 22556853, compound

HRID 351579Notes

Reaction equation

HRID 351579 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:19][CH:20]=[CH2:21])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[NH:17][CH:16]=[CH:15]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:19][CH:20]=[CH2:21])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[N:17]([CH2:26][CH:25]=[CH2:24])[CH:16]=[CH:15]2)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 22556802HCID 22556802, compound

Product 1

HCID 22556853HCID 22556853, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22 °C

Procedure

To a 0° C. solution of N-[tert-butoxycarbonyl]N-allyl N-[(1H-indol-7-yl)methyl]amine (6.6 g, 23 mmol) in anhydrous dimethylformamide was added slowly sodium hydride (60% dispersion in mineral oil, 1.75 g, 43.7 mmol). The mixture was warmed to 20-24° C. and stirred for 30 minutes, followed by the addition of allyl bromide (4.0 mL, 46 mmol). The reaction was then stirred at 20-24° C. overnight. The reaction mixture was diluted with ethyl acetate (450 mL), washed with water (2×100 mL), saturated aqueous sodium chloride (150 mL), and the organic layer dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 10% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 6.8 g (91%) of the desired compound as a light brown oil.

Workup

  1. stirringThe reaction was then stirred at 20-24° C. overnight
  2. washwashed with water (2×100 mL), saturated aqueous sodium chloride (150 mL)
  3. dry with materialthe organic layer dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washeluting with 10% ethyl acetate in hexanes
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d5a4de0e520c46dab704682f8947aa29
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Reaction notes

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