Sodium Carbonate → 3-(3-Nitrophenyl)pyridine

HRID 460192Notes

Reaction equation

HRID 460192 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH: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+]>COCCOC>[N+:8]([C:4]1[CH:3]=[C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 125741-Iodo-3-nitrobenzeneHCID 27343783-Pyridinylboronic acid

Product 1

HCID 121813273-(3-Nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a 1-iodo-3-nitrobenzene (1.0 g, 4.01 mmol) in dry DME (20 mL) was added pyridine-3-boronic acid (641 mg, 5.22 mmol), PdCl2dppf (327 mg, 0.40 mmol), and 2M Na2CO3 (3.0 mL) The resulting mixture was heated to reflux under N2 for 15 h. Solvent was separated from inorganic solid by filtration. The solvent was removed and the residue was extracted with CHCl3. The organic layer was washed with water, brine, and dried over MgSO4. The solvent was removed to give dark brown solid which was purified by chromatography on silica gel. Elution with Hexane:acetone mixture (80:20) gave the final compound as a tan solid. MS m/z: 201.3 (M+H). Calc'd. for C11H8N2O2-200.23.

Workup

  1. temperaturewas heated
  2. temperatureto reflux under N2 for 15 h
  3. customSolvent was separated from inorganic solid by filtration
  4. customThe solvent was removed
  5. extractionthe residue was extracted with CHCl3
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed
  9. customto give dark brown solid which
  10. customwas purified by chromatography on silica gel
  11. washElution with Hexane

Sources & evidence

ORD record
ord-5adce7662513421eb4d2832712721b67
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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