ethyl 4,8-dichloroquinoline-3-carboxylate → HCID 22674078, compound

HRID 1173114Notes

Reaction equation

HRID 1173114 reaction equation
[CH2:1](C([Sn])=C(CCCC)CCCC)[CH2:2]CC.[CH2:16]([O:18][C:19]([C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:30]=1Cl)=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:32])=[O:20])[CH3:17]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH2:16]([O:18][C:19]([C:21]1[CH:22]=[N:23][C:24]2[C:29]([C:30]=1[CH:1]=[CH2:2])=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:32])=[O:20])[CH3:17]

Participants

5

Reactant 2

HCID 728974ethyl 4,8-dichloroquinoline-3-carboxylateHCID 53438229Tri(butyl)vinyltin

Product 1

HCID 22674078HCID 22674078, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Tributylvinyltin (2.8 ml) and tetrakistriphenylphosphinepalladium (171 mg) were added to a toluene solution (20 ml) containing 2.0 g (7.4 mmol) of ethyl-4,8-dichloroquinoline-3-carboxylate obtained in the same manner as in Production Example 4b, followed by stirring for 2 hours under heating under reflux. The reaction solution was filtered through Celite and the filtrate was concentrated. Then, the residue was purified by silica gel chromatography, to give 1.92 g of the title compound.

Workup

  1. customobtained in the same manner as in Production Example 4b
  2. temperatureunder heating
  3. temperatureunder reflux
  4. filtrationThe reaction solution was filtered through Celite
  5. concentrationthe filtrate was concentrated
  6. customThen, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4a43c73c8d4d421c8bda1189aeee0625
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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