Sodium Carbonate → HCID 4184629, compound

HRID 379557Notes

Reaction equation

HRID 379557 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].Cl.Br[C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O.[Pd]>[N:17]1[CH:18]=[CH:19][C:14]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27343264-Cyanophenylboronic acid

Product 1

HCID 4184629HCID 4184629, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4-Cyanophenylboronic acid (1.49 g, 10 mmol), 4-bromopyridine hydrochloride (1.97 g, 10 mmol), 10% palladium-on-carbon (322 mg) and anhydrous sodium carbonate (2.15 g, 20 mmol) were refluxed in a mixture of ethanol (12 mL) and water (3 mL), overnight under an atmosphere of argon. The reaction mixture was filtered through diatomaceous earth, then concentrated in vacuo. The resulting white solid was separated between ethyl acetate (3×100 mL) and water (100 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The resulting solid was subjected to chromatography (SiO2; 50%, 60%, 70%, 80% ethyl acetate/iso-Hexane) to yield 4-(4-pyridyl)benzonitrile a crystalline white solid (1.60 g), 1H NMR (DMSO-d6) δ=7.77 ppm (dd,2H), δ=7.99 ppm (m,4H), δ=8.69 ppm (dd,2H); MS (M+H)+ 181.

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. customThe resulting white solid was separated between ethyl acetate (3×100 mL) and water (100 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03cc70aa7bc6429a9016b1c645a0f6cb
Source dataset
uspto-grants-2001_10
Patent number
US06300330B1

Reaction notes

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