Homoallyl bromide → Methyl 1-but-3-en-1-yl-3-cyclohexyl-2-(2-vinylphenyl)-1H-indole-6-carboxylate

HRID 1714044Notes

Reaction equation

HRID 1714044 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+].Br[CH2:31][CH2:32][CH:33]=[CH2:34]>CN(C=O)C.CCOC(C)=O>[CH2:34]([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])[CH2:33][CH:32]=[CH2:31]

Participants

6

Reactant 3

HCID 21241Homoallyl bromide2×HCID 24758Sodium hydride2×HCID 58765232methyl 3-cyclohexyl-2-(2-vinylphenyl)1H-indole-6-carboxylate

Product 1

HCID 44155798Methyl 1-but-3-en-1-yl-3-cyclohexyl-2-(2-vinylphenyl)-1H-indole-6-carboxylate

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 stirring for 45 min at RT, 4-bromobut-1-ene (1.5 eq) was added and the suspension was stirred for 5 h at 40° C. and then 1 day at RT (NaH and 4-bromobut-1-ene were added several times). The mixture was diluted with EtOAc, washed with 1N HCl, water and brine, dried (Na2SO4) and concentrated in vacuo to give, after chromatography (PE/EtOAc 95:5), the title compound (60%) along with recovered starting material (40%); MS (ES+) m/z 414 (M+H)+.

Workup

  1. stirringthe suspension was stirred for 5 h at 40° C.
  2. washwashed with 1N HCl, water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give
  6. customafter chromatography (PE/EtOAc 95:5), the title compound (60%) along with recovered

Sources & evidence

ORD record
ord-24184463e6da43a4ab53c8318cd2aa5d
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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