Potassium Carbonate → ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)propanoate

HRID 519077Notes

Reaction equation

HRID 519077 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]3)=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(#N)C>[CH3:1][C:2]1[N:3]([C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[N:15]3[CH:26]([CH3:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 867274437-(2,5-dimethyl-pyrrol-1-yl)-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 86727444ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)propanoateYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-(2,5-dimethyl-1H-pyrrol-1-yl)-3,4-dihydroquinolin-2(1H)-one (1.4 g, 5.8 mmol) and potassium carbonate (2.4 g, 17.5 mmol) in ACN (40 mL) was stirred for 30 min then ethyl 2-bromopropanoate (2.1 g, 11.6 mmol) was added and the mixture was heated to reflux overnight. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. EtOAc (50 mL) and water (30 mL) was added to the residue and the organic layer was separated, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether) to give ethyl 2-(7-(2,5-dimethyl-1H-pyrrol-1-yl)-2-oxo-3,4-dihydroquinolin-1(2H)-yl)propanoate (1.6 g, 81%). 1H NMR (CDCl3, 400 MHz): δ 7.26 (d, J=7.2 Hz, 1H), 6.87 (d, J=7.6 Hz, 1H), 6.71 (s, 1H), 5.91 (s, 2H), 4.98 (q, J=6.8 Hz, 1H), 4.17 (q, J=7.2 Hz, 2H), 2.96 (m, 2H), 2.72 (m, 2H), 2.05 (s, 6H), 1.61 (d, J=7.2 Hz, 3H), 1.19 (t, J=7.2 Hz, 3H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. customthe solvent was removed in vacuo
  4. additionEtOAc (50 mL) and water (30 mL) was added to the residue
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on silica gel (eluting with 0-30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-b1381cf3d9844362832465aa3be8a088
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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