Allyl bromide → methyl 1-allyl-3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate

HRID 1444618Notes

Reaction equation

HRID 1444618 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][CH:23]=[CH:22][C:21]=2[CH:26]=[CH2:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH2:30](Br)[CH:31]=[CH2:32]>CN(C=O)C.CCOC(C)=O>[CH2:32]([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][CH:23]=[CH:22][C:21]=1[CH:26]=[CH2:27])[CH:31]=[CH2:30]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 58765232methyl 3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate

Product 1

HCID 58765270methyl 1-allyl-3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0.3M solution of methyl 3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate in dry DMF, 60% NaH (1.5 eq) in mineral oil was added at 0° C., after 1 h allyl bromide (1.5 eq) was added and the suspension was stirred at RT for 2 h. The mixture was diluted with EtOAc, washed with 1N HCl, water and brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (100% as crude); MS (ES+) m/z 400 (M+H)+.

Workup

  1. additionwas added
  2. washwashed with 1N HCl, water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8977ea34df864fe3aa0764a384800ee1
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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