Potassium Carbonate → HCID 69254443, compound

HRID 746758Notes

Reaction equation

HRID 746758 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Br:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 69254443HCID 69254443, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

4-Chloro-3-nitro-pyridine (6.9 g, 43.5 mmol), 4-bromophenyl boronic acid (8.05 g, 40.1 mmol), potassium carbonate (11.10 g, 80.3 mmol) and tetrakis triphenylphosphine palladium (2.31 g, 2.0 mmol) are taken up in DME (200 ml) and heated under reflux (100° C.) overnight. The mixture is cooled down to room temperature and filtered through Celite® pad, which is washed with EtOAc. The filtrate is concentrated to give a crude brown oil. Purification by flash chromatography (Silica gel-hexane/EtOAc) yields 4-(4-Bromo-phenyl)-3-nitro-pyridine (8.52 g) as a yellow oil (76% yield).

Workup

  1. temperatureheated
  2. temperatureThe mixture is cooled down to room temperature
  3. filtrationfiltered through Celite® pad, which
  4. washis washed with EtOAc
  5. concentrationThe filtrate is concentrated
  6. customto give a crude brown oil
  7. customPurification by flash chromatography (Silica gel-hexane/EtOAc)

Sources & evidence

ORD record
ord-5d19f2e2e727481b8d2ffc76f473a5f5
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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