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

HRID 1354186

반응식

HRID 1354186 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9c94fe53bdf64d809ce518414720261c
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223773B2

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