Cesium carbonate → 4-(3-nitrophenyl)pyridine

HRID 1628266Notes

Reaction equation

HRID 1628266 reaction equation
Br[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][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N+:8]([C:4]1[CH:3]=[C:2]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11457Benzene, 1-bromo-3-nitro-HCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acid

Product 1

HCID 4595574-(3-nitrophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a 250 ml flask was added 1-bromo-3-nitrobenzene 34.1.A (500 mg, 2.5 mmol), pyridin-4-ylboronic acid (665 mg, 5.45 mmol), and Pd(Ph3)4 (578 mg, 0.5 mmole), 40 ml of DMF, 10 ml of saturated aqueous sodium bicarbonate and cesium carbonate (1.63 g, 5.0 mmol). The resulting mixture was stirred overnight at 70° C., at which time the reaction mixture was partitioned between 500 ml of EtOAc and 100 ml of water. The organic layer was extracted twice more with 100 ml of water and the organic phase was concentrated to afford 34.1.B which was used in the next step without any further purification.

Workup

  1. customwas partitioned between 500 ml of EtOAc and 100 ml of water
  2. extractionThe organic layer was extracted twice more with 100 ml of water
  3. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-a45d75e0cdd647449eaa0c61ee179221
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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