4-oxo-8-phenylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate → 4-oxo-8-phenethyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970053Notes

Reaction equation

HRID 1970053 reaction equation
[O:1]=[C:2]1[C:11]2[NH:12][CH:13]=[CH:14][C:10]=2[C:9]2[CH:8]=[C:7]([C:15]#[C:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:6]=[CH:5][C:4]=2[NH:3]1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]>[Pd].C(O)C>[O:1]=[C:2]1[C:11]2[NH:12][CH:13]=[CH:14][C:10]=2[C:9]2[CH:8]=[C:7]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:6]=[CH:5][C:4]=2[NH:3]1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]

Participants

4

Reactant 1

HCID 866275534-oxo-8-phenylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275594-oxo-8-phenethyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10 mg of palladium on charcoal is added to a suspension of 14 mg (0.04 mmol) of 4-oxo-8-phenylethynyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in 5 ml of ethanol and the mixture is placed under a hydrogen atmosphere for 24 hours. The raw reaction product is then filtered on celite, and the filtrate is evaporated. The residue is triturated with methanol to give 4 mg (28%) of 4-oxo-8-phenethyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. customThe raw reaction product
  2. filtrationis then filtered on celite
  3. customthe filtrate is evaporated
  4. customThe residue is triturated with methanol

Sources & evidence

ORD record
ord-d5cc4aaab4684a428a798e1f105389db
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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