Potassium Phosphate, Tribasic → 1-{5-chloro-1-[3-(trifluoromethyl)phenyl]-1H-indol-2-yl}heptan-1-one

HRID 1818617노트

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HRID 1818617 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.I[C:20]1[CH:21]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:24][CH:25]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=1)[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 66777278HCID 66777278, 화합물

생성물 1

HCID 667789981-{5-chloro-1-[3-(trifluoromethyl)phenyl]-1H-indol-2-yl}heptan-1-one

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 1140Toluene용매

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온도
110 °C

실험 절차

To a vial containing the title compound of Example 1 Step B (3.0 g, 11.36 mmol), were added 3-iodobenzotrifluoride (1.97 mL, 13.6 mmol), copper iodide (218 mg, 1.14 mmol), potassium phosphate (5.05 g, 23.9 mmol), and 1,2-trans-N,N-dimethylcyclohexane diamine (0.718 mL, 4.54 mmol). The reaction mixture was placed under a nitrogen atmosphere, and anhydrous toluene (11.4 mL, deoxygenated via nitrogen sparge) was added. The vial was then capped and placed in a pre-heated oil bath (110° C.) and stirred rapidly for 19 h. The mixture was allowed to cool to room temperature, then was filtered. The supernatant was washed extensively with EtOAc, and the organic phase was concentrated in vacuo. Purification by flash chromatography (10% EtOAc in hexanes) afforded the title compound: LCMS B, tr=3.02 min, m/z 408.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.74-7.72 (m, 2H), 7.64 (t, J=8.0 Hz, 1H), 7.52 (s, 1H), 7.46 (d, J=8.0 Hz, 1H), 7.37 (s, 1H), 7.26 (dd, J=9.0, 2.0 Hz, 1H), 6.96 (d, J=9.0 Hz, 1H), 2.94 (t, J=7.5 Hz, 2H), 1.68 (quint., J=7.5 Hz, 2H), 1.38-1.28 (m, 6H), 0.88 (t, J=7.0 Hz, 3H).

후처리

  1. customThe vial was then capped
  2. customplaced in a pre-heated oil bath
  3. temperatureto cool to room temperature
  4. filtrationwas filtered
  5. washThe supernatant was washed extensively with EtOAc
  6. concentrationthe organic phase was concentrated in vacuo
  7. customPurification by flash chromatography (10% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-0ea74e0ed2aa4caf9fe0a2ad42eb575d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598398B2

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