Potassium Carbonate → HCID 70663585, compound

HRID 877996Notes

Reaction equation

HRID 877996 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[F:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[C:14]([CH3:21])[CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[F: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])=[C:14]([CH3:21])[CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 70663585HCID 70663585, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-chloro-3-nitropyridine (2.4 g, 15.1 mmol, CAS RN 13091-23-1), 4-fluoro-2-methylphenylboronic acid (2.8 g, 18.2 mmol, CAS RN 139911-29-8), potassium carbonate (6.28 g, 45.4 mmol) and palladium tetrakis-triphenylphosphine (794 mg, 0.76 mmol, CAS RN 14221-01-3) in dioxane (75 mL) was heated to reflux for 16 hours. After cooling to room temperature, the reaction mixture was filtered through Celite and all volatiles were removed under reduced pressure. Column chromatography on silica gel (20-33% EtOAc in n-hexane) afforded 4-(4-fluoro-2-methylphenyl)-3-nitropyridine as a yellow crystalline solid (3.2 g, 90%) which was used in the next step without further purification.

Workup

  1. temperatureto reflux for 16 hours
  2. filtrationthe reaction mixture was filtered through Celite
  3. customall volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-59a533bbd0ae4de38ecdd7cbf5f90adf
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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