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

HRID 1818617ノート

反応式

HRID 1818617 の反応式
[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

参加物

6

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-HCID 667772781-(5-chloro-1H-indol-2-yl)heptan-1-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-0ea74e0ed2aa4caf9fe0a2ad42eb575d
出典データセット
uspto-grants-2009_10
特許番号
US07598398B2

反応ノート

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