Potassium Carbonate → 5-Tert-butyl-2-methyl-3-nitro-pyridine

HRID 735796Notes

Reaction equation

HRID 735796 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[C:8](Cl)=[N:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:15](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.CCOCC>[C:1]([C:5]1[CH:6]=[C:7]([N+:12]([O-:14])=[O:13])[C:8]([CH3:15])=[N:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 222177285-Tert-butyl-2-chloro-3-nitro-pyridine

Product 1

HCID 210243025-Tert-butyl-2-methyl-3-nitro-pyridineYield 77.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-tert-butyl-2-chloro-3-nitro-pyridine (554 mg, 2.58 mmol) dissolved in 10% aqueous dioxane (5.0 mL) was added potassium carbonate (1.07 g, 7.74 mmol), trimethylboroxine (395 mL, 2.84 mmol), and lastly tetrakis-(triphenylphosphine)palladium (149 mg, 0.129 mmol). The solution was heated in a sealed tube to 100° C. for 18 h, cooled to room temperature and diluted with ether. The organic layer was washed twice with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica-gel chromatography (10% ethyl acetate in hexane) provided 5-tert-butyl-2-methyl-3-nitro-pyridine (388 mg, 75%) as colorless oil.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer was washed twice with saturated aqueous NaHCO3
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica-gel chromatography (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-d4ff8d9a59ba4beaaf164dc011e25b62
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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