Potassium Carbonate → Methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylate

HRID 1387961ノート

反応式

HRID 1387961 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5]2.B([O-])([O-])O[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[C:7]([CH3:12])[C:6]([C:13]([O:15][CH3:16])=[O:14])=[CH:5]3)=[CH:20][CH:21]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 18472460Methyl 6-bromo-2-methylquinoline-3-carboxylateHCID 866453334-Methylphenyl borate

生成物 1

HCID 18472437Methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylate収率 100.6%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 66602552Toluene-ethanol water溶媒

実験手順

Under argon atmosphere, a solution of methyl 6-bromo-2-methylquinoline-3-carboxylate (1.22 g), 4-methylphenyl borate (0.65 g) and potassium carbonate (1.18 g) in toluene-ethanol-water (40-4-4 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.15 g), and the mixture was refluxed for 18 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:1) to give methyl 6-(4-methylphenyl)-2-methylquinoline-3-carboxylate (1.27 g) as colorless crystals.

後処理

  1. temperaturethe mixture was refluxed for 18 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:1)

出典と根拠

ORDレコード
ord-29318a8f4ddc4bd08e2bd431eb9edeee
出典データセット
uspto-grants-2001_07
特許番号
US06268354B1

反応ノート

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