Sodium Bicarbonate → 4-Phenyl-3-(1-phenylcyclopropyl)-8-(trifluoromethyl)quinoline

HRID 2104599ノート

反応式

HRID 2104599 の反応式
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]1([C:18]2([CH2:21][CH2:22]O)[CH2:20][CH2:19]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[NH2:24][C:25]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:28]=[CH:27][C:26]=1[C:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CC(O)=O>[C:37]1([C:35]2[C:26]3[C:25](=[C:30]([C:31]([F:32])([F:33])[F:34])[CH:29]=[CH:28][CH:27]=3)[N:24]=[CH:22][C:21]=2[C:18]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:20][CH2:19]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 136403132-(1-Phenylcyclopropyl)ethanolHCID 21555860HCID 21555860、化合物HCID 178418287HCID 178418287、化合物

生成物 1

HCID 669132914-Phenyl-3-(1-phenylcyclopropyl)-8-(trifluoromethyl)quinoline収率 17%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
120 °C

実験手順

Pyridinium chlorochromate (0.417 g, 1.94 mmol) in CH2Cl2 (3 mL) is treated with a mixture of 2-(1-phenylcyclopropyl)ethanol (0.157 g, 0.967 mmol) in CH2Cl2 (2 mL) for 2 h. The reaction is filtered through Celite, treated with AcOH (3 mL) and [2-amino-3-(trifluoromethyl)phenyl](phenyl)methanone (0.128 g, 0.484 mmol), and the methylene chloride is removed in vacuo. Then 1:20H2SO4:AcOH (0.1 mL) is added and the reaction is heated at 120° C. for 3.5 h. The cooled reaction is poured into saturated aq sodium bicarbonate and extracted with ethyl acetate. The extract is washed with saturated aq sodium bicarbonate and dried (MgSO4). The residue is chromatographed eluting with 5:95 ethyl acetate:hexane and then prep HPLC with a gradient of 10-100% acetonitrile/water to afford the title compound (0.032 g). HRMS: calcd for C25H18F3N+H, 390.14696; found (ESI, [M+H]+), 390.1468.

後処理

  1. filtrationThe reaction is filtered through Celite
  2. customthe methylene chloride is removed in vacuo
  3. additionThen 1:20H2SO4:AcOH (0.1 mL) is added
  4. customThe cooled reaction
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with saturated aq sodium bicarbonate
  7. dry with materialdried (MgSO4)
  8. customThe residue is chromatographed
  9. washeluting with 5:95 ethyl acetate

出典と根拠

ORDレコード
ord-9ebad7db2ce2473fbdd434ca636c7445
出典データセット
uspto-grants-2009_08
特許番号
US07576215B2

反応ノート

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