Dichloromethane → 7-[(4'-Tert-butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester

HRID 51920

反応式

HRID 51920 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([NH:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1Br)[CH:10]=2)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].ClCCl.[C:35]([C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1)([CH3:38])([CH3:37])[CH3:36]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[C:11]([NH:16][C:17]([C:18]1[C:19]([C:42]3[CH:43]=[CH:44][C:39]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:40][CH:41]=3)=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:25])[CH:10]=2)=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 698911587-(2-Bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester

生成物 1

HCID 698914667-[(4'-Tert-butyl-biphenyl-2-carbonyl)-amino]-quinoline-3-carboxylic acid ethyl ester収率 87.5%

試薬・触媒・溶媒 2

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 312751,4-Dioxane溶媒

実験手順

To 5 ml dioxane was added in sequence, 7-(2-bromobenzoylamino)quinoline-3-carboxylic acid ethyl ester (100 mg, 0.25 mmol), potassium carbonate (0.25 ml of 2.0M aqueous solution, 0.5 mmol), 1,1′-bis(diphenylphosphino)ferrocene (6.9 mg, 0.0125 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (10.2 mg, 0.0125 mmol) and 4-tert-butylbenzeneboronic acid (111.5 mg, 0.63 mmol). The resulting mixture was degassed and placed under a nitrogen atmosphere. The degassing procedure was repeated 5 times and the reaction mixture was heated under reflux under nitrogen overnight. The reaction mixture was then cooled to room temperature and poured into water. The aqueous mixture was extracted with ethyl acetate and the ethyl acetate solution was washed with brine, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue was purified by preparative thick layer chromatography, eluting with 60:40 hexane/ethyl acetate to yield the title compound (99 mg, 87.3% yield).

後処理

  1. customThe resulting mixture was degassed
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux under nitrogen overnight
  4. additionpoured into water
  5. extractionThe aqueous mixture was extracted with ethyl acetate
  6. washthe ethyl acetate solution was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated to dryness in vacuo
  9. customThe residue was purified by preparative thick layer chromatography
  10. washeluting with 60:40 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-eb795fd21c0d4831bfb772b80a48ee85
出典データセット
uspto-grants-2004_03
特許番号
US06713489B2

関連ノート

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