Cesium carbonate → 5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(4-fluorophenylthio)nicotinonitrile

HRID 916939

반응식

HRID 916939 반응식
Cl[C:2]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[Cl:17])[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[Cs+].[Cs+].[F:31][C:32]1[CH:37]=[CH:36][C:35]([SH:38])=[CH:34][CH:33]=1>C1(C)C=CC=CC=1>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C:7]2[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=3[Cl:17])=[N:9][C:2]([S:38][C:35]3[CH:36]=[CH:37][C:32]([F:31])=[CH:33][CH:34]=3)=[C:3]([CH:6]=2)[C:4]#[N:5])=[CH:19][CH:20]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 677894-FluorothiophenolHCID 101506772-Chloro-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)nicotinonitrile

생성물 1

HCID 103110955-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(4-fluorophenylthio)nicotinonitrile

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

An oven-dried round bottom flask was charged with 60.0 mg (0.152 mmol) of the product of Example 36 and Cs2CO3 (250.0 mg, 0.767 mmol), toluene (1.0 mL) and 4-fluorobenzene thiol (97.5 mg, 0.761 mmol) were added sequentially. The reaction was heated to 100° C. for 23 hours and then allowed to cool to room temperature at which point the reaction was filtered and concentrated. The residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel) eluting with 10:90 EtOAc-hexane affording a white solid). MS (electrospray) m/e 487 MH+.

후처리

  1. additionwere added sequentially
  2. temperatureto cool to room temperature at which
  3. filtrationwas filtered
  4. concentrationconcentrated
  5. customThe residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel)
  6. washeluting with 10:90 EtOAc-hexane affording a white solid)

출처 및 근거

ORD 기록
ord-8914b0d84d26416787fa26fdeba3d078
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271266B2

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