Cesium carbonate → 3-(5-Chloropyridin-3-ylethynyl)-benzonitrile

HRID 606847

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HRID 606847 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1.[C:15]([C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[C:20]#[N:21])#[CH:16].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[Pd](Cl)Cl.C(#N)C.C(#N)C>[Cl:14][C:12]1[CH:13]=[C:8]([C:16]#[C:15][C:17]2[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=2)[C:20]#[N:21])[CH:9]=[N:10][CH:11]=1

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 171533,5-DichloropyridineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 120889643-Ethynylbenzonitrile

생성물 1

HCID 670477693-(5-Chloropyridin-3-ylethynyl)-benzonitrile수율 19%

시약·촉매·용매 1

HCID 6093782Bis(acetonitrile)dichloropalladium촉매

반응 조건

온도
110 °C

실험 절차

Add cesium carbonate (6.59 g, 20.25 mmol) to a degassed mixture of 3,5-dichloropyridine (1 g, 6.75 mmol), 3-ethynylbenzonitrile, (prepared as described in PREPARATION 8), (1.29 g, 10.12 mmol) 2-dicyclohexylphosphino-2′,4′,6′-tri-isopropyl-1,1′-biphenyl (X-PHOS) (96.3 mg, 0.202 mmol) and bis(acetonitrile) palladium (II) chloride (17.5 mg, 0.068). Stir at 110° C. in a sealed tube for 16 h. Cool to room temperature. Quench with water, and extract the product with ethyl acetate. Concentrate and purify the residue by silica gel chromatography, eluting with 100:0 to 100:50 hexanes:ethyl acetate, to give the title compound (300 mg, 19%).

후처리

  1. temperatureCool to room temperature
  2. customQuench with water
  3. extractionextract the product with ethyl acetate
  4. concentrationConcentrate
  5. custompurify the residue by silica gel chromatography
  6. washeluting with 100:0 to 100:50 hexanes

출처 및 근거

ORD 기록
ord-8d3fe9afece94c8fa1a960513ea82c9a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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