Potassium Carbonate → 2-Methyl-3-nitropyridine

HRID 1865178Notes

Reaction equation

HRID 1865178 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11]B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:11][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 139377Methylboronic Acid

Product 1

HCID 3293602-Methyl-3-nitropyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of 2-chloro-3-nitro-pyridine (1a-1, 7.9 g, 49.8 mmol), methylboronic acid (1.10 equiv. 54.8 mmol, 3.30 g), K2CO3 (3.0 equiv, 150 mmol, 20.7 g) and Pd(PPh3)4 (1.2 g, 1.2 mmol) to 110° C. in dioxane (250 mL) for 16 h. Allow the reaction to cool to rt, concentrate to a dark oil and flash chromatograph on SiO2 (heptane/Et2O 3:1, dilute the oil with limited quantities of CH2Cl2 to apply to the column) to give compound 2a-1 (Niu, C.; Li, J.; Doyle, T. W.; Chen, S-H. Tetrahedron, 1998, 6311-6318).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. concentrationconcentrate to a dark oil and flash chromatograph on SiO2 (heptane/Et2O 3:1
  4. additiondilute the oil with limited quantities of CH2Cl2 to apply to the column)
  5. customto give compound 2a-1 (Niu, C.; Li, J.; Doyle, T. W.; Chen, S-H. Tetrahedron, 1998, 6311-6318)

Sources & evidence

ORD record
ord-6a0305fbfec64dc3ba8d59e7e9276179
Source dataset
uspto-grants-2009_12
Patent number
US07626027B2

Reaction notes

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