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

HRID 2104599노트

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HRID 2104599 반응식
[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

참가 물질

7

반응물 4

HCID 516892Sodium BicarbonateHCID 136403132-(1-Phenylcyclopropyl)ethanolHCID 21555860HCID 21555860, 화합물HCID 178418287HCID 178418287, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매2회

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온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ebad7db2ce2473fbdd434ca636c7445
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576215B2

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