Allyl bromide → HCID 67344093, compound

HRID 1669431Notes

Reaction equation

HRID 1669431 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[CH2:28][O:29][Si:30]([CH:37]([CH3:39])[CH3:38])([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:42](Br)[CH:43]=[CH2:44]>CN(C=O)C>[CH2:44]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)[C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[CH2:28][O:29][Si:30]([CH:31]([CH3:32])[CH3:33])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:43]=[CH2:42]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 67345419methyl 3-cyclohexyl-2-(4-methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate

Product 1

HCID 67344093HCID 67344093, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-cyclohexyl-2-(4-methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)-1H-indole-6-carboxylate (1 eq) was dissolved in DMF (0.34M solution) and the solution was degassed. NaH (60% dispersion in mineral oil; 1.1 eq) was added and the mixture was stirred for 5 min. Allyl bromide (1.2 eq) was added and stirring was continued for 5 h. All volatiles were evaporated in vacuo and the residual material was dissolved in Et2O. The solution was washed with 0.5N HCl, saturated aq. NaHCO3 solution and with brine. After drying the organic phase over Na2SO4 all volatiles were evaporated in vacuo and the residual material was purified by FC (PE:EtOAc, 10:1). After evaporation of the solvents the product was obtained as a colourless sticky solid (84%). The material was used without further characterization in the next reaction.

Workup

  1. customthe solution was degassed
  2. stirringstirring
  3. waitwas continued for 5 h
  4. customAll volatiles were evaporated in vacuo
  5. dissolutionthe residual material was dissolved in Et2O
  6. washThe solution was washed with 0.5N HCl, saturated aq. NaHCO3 solution and with brine
  7. dry with materialAfter drying the organic phase over Na2SO4 all volatiles
  8. customwere evaporated in vacuo
  9. customthe residual material was purified by FC (PE:EtOAc, 10:1)
  10. customAfter evaporation of the solvents the product

Sources & evidence

ORD record
ord-7480a6670e76417c968a486ebe7bfc1d
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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