Allyl bromide → HCID 22556853, compound

HRID 910072Notes

Reaction equation

HRID 910072 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]([CH2:21][CH:22]=[CH2:23])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[NH:19][CH:18]=[CH:17]2)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:24](Br)[CH:25]=[CH2:26]>CN(C)C=O.C(OCC)(=O)C>[C:3]([O:7][C:8]([N:10]([CH2:21][CH:22]=[CH2:23])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:20]=1[N:19]([CH2:26][CH:25]=[CH2:24])[CH:18]=[CH:17]2)=[O:9])([CH3:6])([CH3:5])[CH3:4]

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

Slowly add sodium hydride (60% dispersion in mineral oil, 1.75 g, 43.7 mmol) 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. Warm the mixture to 20-24° C., stir for 30 minutes, add allyl bromide (4.0 ml, 46 mmol), and stir the mixture at 20-24° C. overnight. Dilute the reaction mixture with ethyl acetate (450 mL), wash sequentially with water (2×100 mL) and saturated aqueous sodium chloride (150 mL), dry over sodium sulfate, filter, and concentrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with 10% ethyl acetate in hexanes. Combine fractions containing product and concentrate them under reduced pressure to provide the desired compound as a light brown oil (6.8 g, 91%).

Workup

  1. customto a 0° C.
  2. stirringstir the mixture at 20-24° C. overnight
  3. washwash sequentially with water (2×100 mL) and saturated aqueous sodium chloride (150 mL)
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. washeluting with 10% ethyl acetate in hexanes
  8. additionCombine fractions containing product
  9. concentrationconcentrate them under reduced pressure

Sources & evidence

ORD record
ord-57561222ed154a458f0e7916676229f8
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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