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

HRID 1354186

反応式

HRID 1354186 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9c94fe53bdf64d809ce518414720261c
出典データセット
uspto-grants-2007_05
特許番号
US07223773B2

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