Ethanol → HCID 23019651, compound

HRID 1354192Notes

Reaction equation

HRID 1354192 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[O:12][CH3:13])=[C:9]([CH:14]1[CH2:16][CH2:15]1)[CH:8]=[C:7]([C:17]([O:19]CC)=[O:18])[C:6]2=[O:22].C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[CH3:32][N:33]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1B(O)O)[CH3:34]>C1(C)C=CC=CC=1.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.C(OCC)(=O)C>[CH:14]1([C:9]2[CH:8]=[C:7]([C:17]([OH:19])=[O:18])[C:6](=[O:22])[N:5]3[C:10]=2[C:11]([O:12][CH3:13])=[C:2]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[CH2:35][N:33]([CH3:34])[CH3:32])[CH:3]=[CH:4]3)[CH2:15][CH2:16]1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2734345{2-[(Dimethylamino)methyl]phenyl}boronic acidHCID 18629332HCID 18629332, compound

Product 1

HCID 23019651HCID 23019651, compoundYield 48.4%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

100 mg of ethyl 8-chloro-1-cyclopropyl-9-methoxy-4-oxo-4H-quinolizine-3-carboxylate was suspended in 1 ml of toluene. 0.5 ml of ethanol, 0.25 ml of 2 M aqueous sodium carbonate solution, 61 mg of 2-(N,N-dimethylaminomethyl)phenylboronic acid and 10 mg of bis(triphenylphosphine)palladium (II) chloride were added to the obtained solution, and they were heated under reflux in argon atmosphere for 38 hours. Ethyl acetate was added to the reaction mixture. The organic layer was taken, washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resultant residue was purified by the silica gel column chromatography (eluent: chloroform/acetone=4/1) to obtain 59 mg of 1-cyclopropyl-8-(2-dimethylaminomethylphenyl)-9-methoxy-4-oxo-4H-quinolizine-3-carboxylic acid.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux in argon atmosphere for 38 hours
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resultant residue was purified by the silica gel column chromatography (eluent: chloroform/acetone=4/1)

Sources & evidence

ORD record
ord-f1882f7fc7bb45fdb1a42ff274953f73
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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