Sodium hydride → HCID 22024972, compound

HRID 1792817Notes

Reaction equation

HRID 1792817 reaction equation
[H-].[Na+].[CH:3]1([C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][NH:9][CH:10]=2)[CH2:5][CH2:4]1.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[CH:18][CH:17]=1>CN(C)C=O.[Cl-].[Na+].O>[CH:3]1([C:6]2[C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][N:9]([C:16]3[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=[CH:18][CH:17]=3)[CH:10]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 691404-ChloroquinolineHCID 22024944Methyl 4-cyclopropyl-1H-pyrrole-3-carboxylate

Product 1

HCID 22024972HCID 22024972, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
40 °C

Procedure

0.208 g (6.5 mmol) of sodium hydride at 75% by weight in liquid petroleum jelly is added to a solution of 1.07 g (6.5 mmol) of 4-cyclopropyl-3-methoxycarbonyl-1H-pyrrole in 20 mL of dimethylformamide at a temperature in the region of 20° C. under an argon atmosphere. After the reaction mixture has been stirred at a temperature in the region of 40° C. for 0.3 hour, 1.07 g (6.5 mmol) of 4-chloroquinoline and 10 mL of dimethylformamide are added. After stirring for 6 hours at a temperature in the region of 120° C., the reaction mixture is poured into 200 mL of brine and then extracted with 100 mL and then 50 mL of ethyl acetate. The organic extracts are combined and then concentrated to dryness under reduced pressure (2.7 kPa). The oily residue is purified by chromatography on silica gel [eluent: dichloromethane/ethyl acetate (75/25 by volume)]. After the fractions containing the expected product have been concentrated to dryness under reduced pressure (2.7 kPa), 1.2 g of 4-cyclopropyl-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-pyrrole are obtained in the form of a thick clear oil, which is used directly in the following step.

Workup

  1. stirringAfter stirring for 6 hours at a temperature in the region of 120° C.
  2. extractionextracted with 100 mL
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe oily residue is purified by chromatography on silica gel [eluent: dichloromethane/ethyl acetate (75/25 by volume)]
  5. additionAfter the fractions containing the expected product
  6. concentrationhave been concentrated to dryness under reduced pressure (2.7 kPa), 1.2 g of 4-cyclopropyl-3-methoxycarbonyl-1-(quinolin-4-yl)-1H-pyrrole
  7. customare obtained in the form of a thick clear oil, which

Sources & evidence

ORD record
ord-0ef7b04f28b2421da6aa4ad91d5e166b
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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