Sodium hydride → Ethyl 2-methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylate

HRID 1792788Notes

Reaction equation

HRID 1792788 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][NH:8][C:7]=1[CH3:11])=[O:5])[CH3:2].[H-].[Na+].Cl[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][CH:16]=1>CN(C)C=O.O.[Cu]>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[C:7]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 691404-ChloroquinolineHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylate

Product 1

HCID 22024986Ethyl 2-methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylateYield 103.6%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

2.75 g (17.9 mmol) of 3-ethoxycarbonyl-2-methyl-1H-pyrrole are added at 20° C. under an argon atmosphere to 0.756 g (18.9 mmol) of sodium hydride, at 60% by weight in liquid petroleum jelly, suspended in 12 mL of dimethylformamide. After stirring at 20° C. for 0.2 hour, 0.114 g (1.79 mmol) of copper powder and 2.35 mL (17.9 mmol) of 4-chloroquinoline are added. After stirring at 140° C. for 48 hours, the reaction mixture is filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa) to give a residue which is taken up in 100 mL of water and then extracted with 3 times 70 mL of ethyl acetate. The organic phases are combined, dried over anhydrous magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) to give 5.2 g of a brown oil which is purified by flash chromatography [eluent: dichloromethane/ethyl acetate (97/3 by volume)]. After concentrating the fractions under reduced pressure (2.7 kPa), 3 g of 3-ethoxycarbonyl-2-methyl-1-(quinol-4-yl)-1H-pyrrole are obtained in the form of an orange-coloured oil. Mass spectrum (EI): m/e 280 (M+.), m/e 251, m/e 235.

Workup

  1. stirringAfter stirring at 140° C. for 48 hours
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  4. customto give a residue which
  5. extractionextracted with 3 times 70 mL of ethyl acetate
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-d88754c9caf5409f8c983d0f3a3e0b16
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

Loading…