Benzene → 5-Phenylpyridine-2-carbonitrile

HRID 1858014Notes

Reaction equation

HRID 1858014 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC=CC=1>C(P[Pd](PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)PC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>[C:10]1([C:2]2[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 241BenzeneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 8171545-Bromopyridine-2-carbonitrile

Product 1

HCID 9352765-Phenylpyridine-2-carbonitrileYield 136.7%

Reagents, catalysts & solvents 2

HCID 178420430HCID 178420430, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture comprising 5-bromopyridine-2-carbonitrile (0.09 g, 0.49 mmol), phenyl boronic acid (0.12 g, 0.98 mmol), 2M sodium carbonate ((0.98 mL, 1.96 mmol), tetrakis(tritylphosphanyl)palladium (0.06 g, 0.049 mmol), benzene (2 mL) and ethanol (2 mL) was heated at reflux for 1 hour and then partitioned between ethyl acetate and water. The organic layer was separated, washed with water, dried (MgSO4) and concentrated. The residue was purified by silica gel chromatography (25% ethyl acetate/hexanes) to provide 5-phenylpyridine-2-carbonitrile (0.12 g, 0.67 mmol). MS (CI), Calculated for C12H8N2, 180.2, Found (MH+): 182.

Workup

  1. temperatureat reflux for 1 hour
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-96de982658ac4e01a4410be3ef68cd39
Source dataset
uspto-grants-2000_11
Patent number
US06150379

Reaction notes

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