Sodium Chloride → (E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic acid methyl ester

HRID 352096Notes

Reaction equation

HRID 352096 reaction equation
[CH3:1][O:2][C:3](=[O:39])[CH:4]=[C:5]([O:33]C(OCC)=O)[CH2:6][CH:7](OC(OCC)=O)[C:8]1[N:9]([CH:24]([CH3:26])[CH3:25])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[Cl-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:39])[CH2:4][C:5](=[O:33])/[CH:6]=[CH:7]/[C:8]1[N:9]([CH:24]([CH3:25])[CH3:26])[C:10]2[C:15]([C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 698909703,5-bis-ethoxycarbonyloxy-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-pent-2-enoic acid methyl ester

Product 1

HCID 11326444(E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 100 ml three-necked, round-bottomed flask, equipped with a magnetic stirrer, thermometer, reflux condenser and nitrogen delivery line, 2.17 g of crude 3,5-bis-ethoxycarbonyloxy-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-pent-2-enoic acid methyl ester are dissolved in 50 ml of DMF, 1.0 g of pyridinium p-toluenesulfonate is added and stirring is carried out for 4 hours at 80° C. The reaction mixture is then cooled, poured into 150 ml of saturated sodium chloride solution and extracted four times with 50 ml of ethyl acetate. The combined organic phases are washed six times with 50 ml of water, dried over magnesium sulfate, filtered and concentrated by evaporation. The crude product (brownish-orange resin) is purified by means of flash chromatography (hexane/ethyl acetate=10:1). An orange resin is obtained which, according to NMR, is the product in a keto-enol equilibrium of approximately 3:1.

Workup

  1. customIn a 100 ml three-necked, round-bottomed flask, equipped with a magnetic stirrer
  2. temperaturethermometer, reflux condenser
  3. temperatureThe reaction mixture is then cooled
  4. extractionextracted four times with 50 ml of ethyl acetate
  5. washThe combined organic phases are washed six times with 50 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customThe crude product (brownish-orange resin) is purified by means of flash chromatography (hexane/ethyl acetate=10:1)
  10. customAn orange resin is obtained which

Sources & evidence

ORD record
ord-c0c52351932641f49f84e704163aaf3c
Source dataset
uspto-grants-2004_06
Patent number
US06743926B2

Reaction notes

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