p-Toluenesulfonic acid → HCID 23513934, compound

HRID 353479Notes

Reaction equation

HRID 353479 reaction equation
C([O:4][CH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:23](=[O:33])[C:24]([NH:26][C:27]1[CH2:28][O:29][C:30](=[O:32])[CH:31]=1)=[O:25])=[CH:9][N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)C=C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.O.CCCCCC.CCOC(C)=O.CN(C=O)C.CCO.[Pd]>[Cl:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:10]2[C:11]3[C:7](=[C:6]([CH2:5][OH:4])[CH:14]=[CH:13][CH:12]=3)[C:8]([C:23](=[O:33])[C:24]([NH:26][C:27]3[CH2:28][O:29][C:30](=[O:32])[CH:31]=3)=[O:25])=[CH:9]2)=[CH:21][CH:20]=1

Participants

8

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 23514053HCID 23514053, compound

Product 1

HCID 23513934HCID 23513934, compoundYield 22.9%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

2-[4-[(allyloxy)methyl]-1-(4-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamide (239 mg) is dissolved in MeOH/H2O=9/1 (10 ml) then 10% Pd/C (12 mg) and p-toluenesulfonic acid (12 mg) are added. The reaction is refluxed for about 6 h, then it is diluted with DMF and EtOH, the catalyst is filtered on celite and the solvent is removed under reduced pressure. The crude is washed with acetone and filtered. The filtrate is concentrated and the obtained solid is purified by silica gel chromatography (eluent: CH2Cl2/EtOH=95/5) affording 50 mg of pure 2-[1-(4-chlorobenzyl)-4-(hydroxymethyl)-1H-indol-3-yl]-2-oxo-N-(5-oxo-2,5-dihydro-3-furanyl)acetamide. The solid is crystallized from CH3CN affording 63 mg of compound with m.p. 238-240° C.

Workup

  1. temperatureThe reaction is refluxed for about 6 h
  2. filtrationthe catalyst is filtered on celite
  3. customthe solvent is removed under reduced pressure
  4. washThe crude is washed with acetone
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customthe obtained solid is purified by silica gel chromatography (eluent: CH2Cl2/EtOH=95/5)

Sources & evidence

ORD record
ord-c97bcccf211c41aab48f93d45150c6a3
Source dataset
uspto-grants-2004_06
Patent number
US06753342B2

Reaction notes

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