Cesium carbonate → 3-Trifluoromethyl-5-phenylethynylpyridine

HRID 606845

반응식

HRID 606845 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 670477033-Trifluoromethyl-5-phenylethynylpyridine수율 10%

시약·촉매·용매 3

HCID 6093782Bis(acetonitrile)dichloropalladium촉매HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c56a8d459fa94d37b179bea42a95c2e4
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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