Cesium carbonate → 3-Trifluoromethyl-5-phenylethynylpyridine

HRID 606845

反応式

HRID 606845 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:13]=1.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.O.CC#N.CC#N.Cl[Pd]Cl>[F:15][C:14]([F:17])([F:16])[C:12]1[CH:11]=[N:10][CH:9]=[C:8]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:13]=1

参加物

7

反応物 3

HCID 10796Cesium carbonateHCID 10821PhenylacetyleneHCID 27366983-Chloro-5-(trifluoromethyl)pyridine

生成物 1

HCID 670477033-Trifluoromethyl-5-phenylethynylpyridine収率 10%

試薬・触媒・溶媒 3

HCID 6093782Bis(acetonitrile)dichloropalladium触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

Charge a sealed tube under a positive pressure of argon with bis(acetonitrile)palladium (II) chloride (18 mg, 0.07 mmol), 2-dicyclohexylphosphino diphenyl (73 mg, 0.21 mmol), cesium carbonate (0.557 g, 1.71 mmol) and 3-chloro-5-trifluoromethylpyridine, (prepared essentially as described in PREPARATION 7), (0.12 g, 0.66 mmol) in acetonitrile and stir at room temperature for 25 min (Angew. Chem. Int. Ed. 42, 5993-5996, (2003)). Add phenylacetylene (0.1 mL, 0.86 mmol) and stir at 100° C. for 16 h. Cool to room temperature, dilute with water, and wash twice with ethyl acetate. Combine the ethyl acetate layers, dry (sodium sulfate), and concentrate. Purify the residue by silica gel chromatography, eluting with 100:0 to 50:50 hexanes:dichloromethane, to obtain the title compound (30 mg, 10%).

後処理

  1. custom(prepared essentially
  2. temperatureCool to room temperature
  3. washwash twice with ethyl acetate
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 100:0 to 50:50 hexanes

出典と根拠

ORDレコード
ord-c56a8d459fa94d37b179bea42a95c2e4
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

関連ノート

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