Ethanol → ethyl 8-(3-aminophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

HRID 1354186Notes

Reaction equation

HRID 1354186 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]2[C:10]([C:11]=1[CH3:12])=[C:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]2=[O:21].C(O)C.C(=O)([O-])[O-].[Na+].[Na+].Cl.[NH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1>C1(C)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C>[NH2:32][C:33]1[CH:38]=[C:37]([C:2]2[CH:3]=[CH:4][N:5]3[C:10]([C:11]=2[CH3:12])=[C:9]([CH:13]2[CH2:15][CH2:14]2)[CH:8]=[C:7]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]3=[O:21])[CH:36]=[CH:35][CH:34]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27632413-Aminophenylboronic acid hydrochlorideHCID 12071709ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 9968953ethyl 8-(3-aminophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylateYield 48.4%

Reagents, catalysts & solvents 3

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

Procedure

92.7 mg of ethyl 8-chloro-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate was suspended in 1 ml of toluene. 0.5 ml of ethanol, 0.5 ml of 2 M aqueous sodium carbonate solution, 50 mg of 3-aminophenylboronic acid hydrochloride and 10 mg of bis(triphenylphosphine) palladium (II) chloride were added to the obtained suspension, and they were heated under reflux in argon atmosphere for 3 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/ethyl acetate=4/1) to obtain 50.6 mg of ethyl 8-(3-aminophenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux in argon atmosphere for 3 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/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-9c94fe53bdf64d809ce518414720261c
Source dataset
uspto-grants-2007_05
Patent number
US07223773B2

Reaction notes

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