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

HRID 1970061Notes

Reaction equation

HRID 1970061 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:17]1[CH:26]=[CH:25][C:24]2[NH:23][C:22](=[O:27])[C:21]3[NH:28][CH:29]=[CH:30][C:20]=3[C:19]=2[CH:18]=1.[CH2:31]([C:33]([O-:35])=[O:34])[CH3:32].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[O:27]=[C:22]1[C:21]2[NH:28][CH:29]=[CH:30][C:20]=2[C:19]2[CH:18]=[C:17]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:26]=[CH:25][C:24]=2[NH:23]1.[CH2:31]([C:33]([O-:35])=[O:34])[CH3:32]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 866275178-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275684-oxo-8-phenyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 19.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

17 mg (0.025 mmol) of dichlorobis(triphenylphosphine)-palladium (II), 45 mg (0.37 mmol) of phenylboronic acid and 0.6 mL (1.2 ml) of a 2M aqueous solution of potassium carbonate are added to a degassed solution of 100 mg (0.25 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate dissolved in 5 mL of anhydrous dioxan. The reaction mixture is stirred at 110° C. for 20 hours. Water is added and the product is extracted with ethyl acetate. The organic phases are washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered and evaporated. The residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2) then triturated in methanol to give 16 mg (19%) of 4-oxo-8-phenyl-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic phases are washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2)
  7. customthen triturated in methanol

Sources & evidence

ORD record
ord-d03b0466a25f4ae9b359c393d2d794e4
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

Loading…