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

HRID 916939

反応式

HRID 916939 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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+.

後処理

  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)

出典と根拠

ORDレコード
ord-8914b0d84d26416787fa26fdeba3d078
出典データセット
uspto-grants-2007_09
特許番号
US07271266B2

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