Thiophenol → HCID 86627567, compound

HRID 1970060Notes

Reaction equation

HRID 1970060 reaction equation
I[C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[NH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[CH:3]=1.[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17].C(=O)([O-])[O-].[K+].[K+].[C:27]1([SH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(COC)OC.[Cu](I)I>[O:12]=[C:7]1[C:6]2[NH:13][CH:14]=[CH:15][C:5]=2[C:4]2[CH:3]=[C:2]([S:33][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:11]=[CH:10][C:9]=2[NH:8]1.[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 86627515HCID 86627515, compound

Product 1

HCID 86627567HCID 86627567, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

In a sealed tube, a suspension of 152 mg (0.4 mmol) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate (synthesis 209) and 110 mg (0.8 mmol) of potassium carbonate in dimethoxyethane (0.6 mL) is purged with an argon stream before adding 15 mg (0.08 mmol) of copper iodide and 86 mg (0.6 mmol) of thiophenol. The reaction mixture is heated at 90° C. for 5 to 6 days then filtered on celite and rinsed with dichloromethane, then methanol. The filtrate is evaporated and the residue obtained is purified by chromatography on silica (eluent dichloromethane/methanol 96/4 then 9/1) to give 42 mg (29%) of 4-oxo-8-phenylsulfanyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customis purged with an argon stream
  2. filtrationthen filtered on celite
  3. washrinsed with dichloromethane
  4. customThe filtrate is evaporated
  5. customthe residue obtained
  6. customis purified by chromatography on silica (eluent dichloromethane/methanol 96/4

Sources & evidence

ORD record
ord-528187b68bac41e6a5defc9f71710f40
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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