Tetraethyltin → 8-Ethyl-2-methylquinoline-4-carboxylic Acid Ethyl Ester

HRID 47435

Reaction equation

HRID 47435 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[C:11](Br)[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[CH:7]=1)=[O:5])[CH3:2].[Cl-].[Li+].[CH2:20]([Sn](CC)(CC)CC)[CH3:21]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:1]([O:3][C:4]([C:6]1[C:15]2[C:10](=[C:11]([CH2:20][CH3:21])[CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:17])[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 11704TetraethyltinHCID 433294Lithium ChlorideHCID 698313558-Bromo-2-methylquinoline-4-carboxylic Acid Ethyl Ester

Product 1

HCID 544927358-Ethyl-2-methylquinoline-4-carboxylic Acid Ethyl EsterYield 52%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

8-Bromo-2-methylquinoline4-carboxylic acid ethyl ester (0.5 g), lithium chloride (0.216 g), tetraethyltin (0.435 g) and bis(triphenylphosphine)palladium (II) chloride (0.05 g) were combined in dimethylformamide (20 ml) and heated at 100° C. for 24 h. Solvent was removed at reduced pressure, the residue dissolved in dichloromethane and filtered. Solvent was removed at reduced pressure and the residue column chromatographed (silica gel, 5% diethyl ether/pentane) to give the title compound (0.215 g). m/z (API+): 244 (MH+).

Workup

  1. customSolvent was removed at reduced pressure
  2. dissolutionthe residue dissolved in dichloromethane
  3. filtrationfiltered
  4. customSolvent was removed at reduced pressure
  5. customthe residue column chromatographed (silica gel, 5% diethyl ether/pentane)

Sources & evidence

ORD record
ord-26d0a82c2dfb4cb4aa849e059193991f
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Linked notes

Loading…