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

HRID 606847Notes

Reaction equation

HRID 606847 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalyst

Conditions

Temperature
110 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-8d3fe9afece94c8fa1a960513ea82c9a
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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