Sodium Carbonate → 4-Nitro-2,3′-bipyridine

HRID 1640110Notes

Reaction equation

HRID 1640110 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)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>[N+:8]([C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 7351522-Chloro-4-nitropyridineHCID 27343783-Pyridinylboronic acid

Product 1

HCID 120729174-Nitro-2,3′-bipyridineYield 70%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-chloro-4nitropyridine (0.40 g, 2.56 mmol), pyridin-3-ylboronic acid (0.408, 3.32 mmol), tetrakis(triphenylphosphinepalladium(0) (0.18 g, 0.15 minol) and sodium carbonate (0.489 g, 4.6 mmol) in acetonitrile (9 mL) and water (9 mL) was heated at 80° C. overnight. Water was added and the mixture was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography on basic alumina to give 4-nitro-2,3′-bipyridine (350 mg, 70%) as a pale yellow solid. LCMS: (FA) ES+ 202.1.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on basic alumina

Sources & evidence

ORD record
ord-d45064f7ada44bfbb0adc1212742abf0
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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