Potassium Carbonate → 2-Phenylpyridine-3-carbonitrile

HRID 1058317Notes

Reaction equation

HRID 1058317 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:10]1([C:2]2[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 810792-Chloronicotinonitrile

Product 1

HCID 181776872-Phenylpyridine-3-carbonitrileYield 94.7%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-chloro-3-cyanopyridine (4.06 g, 29.3 mmol) in toluene (60 mL) was added phenylboronic acid (5.4 g, 43.9 mmol), potassium carbonate (6.1 g, 44.1 mmol) and tetrakis(triphenylphosphine)palladium (1.7 g, 1.5 mmol). The mixture was refluxed under nitrogen for 24 hours, then the solvent was removed under reduced pressure. The residue was purified on a silica gel column using 100% CH2Cl2 then 99:1 CH2Cl2:MeOH as mobile phase. Pure fractions were combined and dried in vacuo to yield the solid 2-phenyl-3 cyanopyridine (5.0 g, HPLC RT=2.98 min, method A; LC-MS m/z=181).

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 24 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified on a silica gel column
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f792b1e6072d42abadf838c0838e83cc
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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