1-Bromonaphthalene → 8-naphthalen-1-yl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1970069Notes

Reaction equation

HRID 1970069 reaction equation
C(N(CC)CC)C.Br[C:9]1[CH:18]=[CH:17][C:16]2[NH:15][C:14](=[O:19])[C:13]3[NH:20][CH:21]=[CH:22][C:12]=3[C:11]=2[CH:10]=1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24].Br[C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1.[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+]>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>[C:37]1([C:9]2[CH:18]=[CH:17][C:16]3[NH:15][C:14](=[O:19])[C:13]4[NH:20][CH:21]=[CH:22][C:12]=4[C:11]=3[CH:10]=2)[C:38]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][CH:36]=1.[CH2:23]([C:25]([O-:27])=[O:26])[CH3:24]

Participants

8

Reactant 4

HCID 70011-BromonaphthaleneHCID 8471TriethylamineHCID 61695Pentapotassium TriphosphateHCID 866275178-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275758-naphthalen-1-yl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 14.4%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalyst2×HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

68 mg (0.1 mmol) of dichlorobis(triphenylphosphine)-palladium (11), 149 mg (0.59 mmol) of bis(pinacolo)diborane and 273 μL (1.96 mmol) of triethylamine 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 4 mL of anhydrous dioxan. The reaction mixture is stirred at 110° C. for 4 days. 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 taken up in 5 mL of anhydrous dioxan. The solution is degassed with a stream of nitrogen before adding 81 μL (0.59 mmol) of 1-bromonaphthalene, 69 mg (0.1 mmol) of dichlorobis(triphenylphosphine)-palladium (II) and 1 mL (2 mmol) of a 2M aqueous solution of tribasic potassium triphosphate. 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 (3% in two stages) of 8-naphthalen-1-yl-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a beige 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 solution is degassed with a stream of nitrogen
  7. stirringThe reaction mixture is stirred at 110° C. for 20 hours
  8. extractionthe product is extracted with ethyl acetate
  9. washThe organic phases are washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated
  13. customThe residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-731f18ccce414150b6edc12a67157b7b
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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