3-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole-2-carbaldehyde → (E)-5-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic Acid Ethyl Ester

HRID 1272583Notes

Reaction equation

HRID 1272583 reaction equation
[O:1]=[C:2](C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][C:4]([O-])=O.[F:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]([CH:43]([CH3:45])[CH3:44])[C:35]=2C=O)=[CH:30][CH:29]=1.CCCCCC.[CH2:54]([O:56][C:57](=[O:59])[CH3:58])[CH3:55]>C(#N)C>[CH2:54]([O:56][C:57](=[O:59])[CH2:58][C:2](=[O:1])/[CH:3]=[CH:4]/[C:35]1[N:36]([CH:43]([CH3:44])[CH3:45])[C:37]2[C:42]([C:34]=1[C:31]1[CH:32]=[CH:33][C:28]([F:27])=[CH:29][CH:30]=1)=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH3:55]

Participants

5

Reactant 3

HCID 113120613-(4-Fluorophenyl)-1-(1-methylethyl)-1H-indole-2-carbaldehydeHCID 184577483-Oxo-4-(triphenylphosphoranylidene)butanoateHCID 21226206Ethyl acetate hexane

Product 1

HCID 20730393(E)-5-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The ylide 3-oxo-4-(triphenylphosphoranylidene)butanoate (5.0 g, 12.8 mmol) is solved under argon atmosphere in 100 ml acetonitrile. Under vigorous stirring 3-(4-Fluoro-phenyl)-1-isopropyl-1H-indole-2-carbaldehyde (4.2 g, 10.7 mmol) is added in 5 portions and then heated to reflux. After 50 h the reaction is cooled to room temperature. The slight brown solvent is evaporated and the residue is dried under vacuum to obtain a brown waxy oil. Chromatography over silica gel with hexane:ethylacetate (4:1/v:v) give a yellow oil of (E)-5-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-oxo-pent-4-enoic acid ethyl ester. MS: 393.46

Workup

  1. additionis added in 5 portions
  2. temperatureheated to reflux
  3. customThe slight brown solvent is evaporated
  4. customthe residue is dried under vacuum
  5. customto obtain a brown waxy oil

Sources & evidence

ORD record
ord-2c1a5c9e6d16422bb69ba5bb16e8c048
Source dataset
uspto-grants-2007_04
Patent number
US07208623B2

Reaction notes

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