Sodium Carbonate → 6-Phenylpyridine-3-carbonitrile

HRID 1181029Notes

Reaction equation

HRID 1181029 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6](Cl)=[N:7][CH:8]=1)#[N:2].[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.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:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 125765186-Phenylpyridine-3-carbonitrileYield 94%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Cyano-2-chloropyridine (5.0 g, 36.1 mmol), phenylboronic acid (6.6 g, 54 mmol), tetrakis(triphenylphosphine)palladium (0) (0.5 g), and aqueous Na2CO3 (7.6 g), in toluene (100 mL) were heated at 90° C. for 16 h. The mixture was diluted with EtOAc and washed with H2O. The organic layer was dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography (hexanes/EtOAc 2/1) to afford the title compound (6.1 g, 94%). MS (ESI) m/z 181 (M+H)+.

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (hexanes/EtOAc 2/1)

Sources & evidence

ORD record
ord-e9fd99ab17214f9e8628f736d755ad0d
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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