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

HRID 1970062Notes

Reaction equation

HRID 1970062 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].Br[C:30]1[CH:39]=[CH:38][C:37]2[NH:36][C:35](=[O:40])[C:34]3[NH:41][CH:42]=[CH:43][C:33]=3[C:32]=2[CH:31]=1.[CH2:44]([C:46]([O-:48])=[O:47])[CH3:45].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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:30]1[CH:39]=[CH:38][C:37]2[NH:36][C:35](=[O:40])[C:34]3[NH:41][CH:42]=[CH:43][C:33]=3[C:32]=2[CH:31]=1.[CH2:44]([C:46]([O-:48])=[O:47])[CH3:45]

Participants

7

Reactant 4

HCID 962WaterHCID 61695Pentapotassium TriphosphateHCID 27343222-Chlorophenylboronic acidHCID 866275178-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275698-(2-chlorophenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 15%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

68 mg (0.01 mmol) of dichlorobis(triphenylphosphine)-palladium (II), 92 mg (0.59 mmol) of 2-chlorophenylboronic acid and 1 mL (2 mmol) of a 2M aqueous solution of tribasic potassium triphosphate are added to a degassed solution of 200 mg (0.49 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate dissolved in 10 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) to give 27 mg (15%) of 8-(2-chlorophenyl)-4-oxo-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)

Sources & evidence

ORD record
ord-c00fd13419454634952747e4493f7559
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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