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

HRID 1970066Notes

Reaction equation

HRID 1970066 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:22]=[CH:21][C:20]2[NH:19][C:18](=[O:23])[C:17]3[NH:24][CH:25]=[CH:26][C:16]=3[C:15]=2[CH:14]=1.[CH2:27]([C:29]([O-:31])=[O:30])[CH3:28].[O-]P(OP(OP([O-])([O-])=O)([O-])=O)(=O)[O-].[K+].[K+].[K+].[K+].[K+].O.[CH3:51][NH:52][CH3:53]>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>[CH3:51][N:52]([CH2:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:22]=[CH:21][C:20]3[NH:19][C:18](=[O:23])[C:17]4[NH:24][CH:25]=[CH:26][C:16]=4[C:15]=3[CH:14]=2)[CH:6]=[CH:7][CH:8]=1)[CH3:53].[CH2:27]([C:29]([O-:31])=[O:30])[CH3:28]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 962WaterHCID 61695Pentapotassium TriphosphateHCID 27732813-(Bromomethyl)benzeneboronic acidHCID 866275178-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

Product 1

HCID 866275748-(3-dimethylaminomethyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 10%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

In a sealed tube, 30 mg (0.14 mmol) of 3-bromomethylphenylboronic acid is dissolved in 100 μL of a 40% aqueous solution of dimethylamine and the solution is heated at 100° C. for 4 hours. The solvents are evaporated and the residue is taken up in 1.5 mL of anhydrous dioxan. The solution is degassed before adding 38 mg (0.14 mmol) of 8-bromo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate, 13 mg (0.028 mmol) of dichlorobis(triphenylphosphine)-palladium (11) and 200 μL (0.4 mmol) of a 2M aqueous solution of tribasic potassium triphosphate. The reaction mixture is stirred at II 0° 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 chloroform/methanol/ammonia 90/25/4) to give 5 mg (10%) of 8-(3-dimethylaminomethyl-phenyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a beige solid.

Workup

  1. customThe solvents are evaporated
  2. customThe solution is degassed
  3. extractionthe product is extracted with ethyl acetate
  4. washThe organic phases are washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by chromatography on silica (eluent chloroform/methanol/ammonia 90/25/4)

Sources & evidence

ORD record
ord-5cdfbbb629994d2eb14e4ab9a8247351
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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