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

HRID 606847ノート

反応式

HRID 606847 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 670477693-(5-Chloropyridin-3-ylethynyl)-benzonitrile収率 19%

試薬・触媒・溶媒 1

HCID 6093782Bis(acetonitrile)dichloropalladium触媒

反応条件

温度
110 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-8d3fe9afece94c8fa1a960513ea82c9a
出典データセット
uspto-grants-2011_03
特許番号
US07915424B2

反応ノート

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