Sodium Carbonate → HCID 13734413, compound

HRID 1014183Notes

Reaction equation

HRID 1014183 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(O)O)[CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C(OCC)(=O)C>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1185334-Bromo-2-nitroanisoleHCID 27343783-Pyridinylboronic acid

Product 1

HCID 13734413HCID 13734413, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Nitrogen was bubbled through dioxane (100 mL) followed by the addition of 4-bromo-1-(methyloxy)-2-nitrobenzene (5.0 g, 21.55 mmol, Transworld). To the solution were added 3-pyridinylboronic acid (3.16 g, 25.90 mmol, Boron Molecular), dichloro(triphenylphosphine)palladium (0.76 g, 1.08 mmol, Strem) and degassed aqueous Na2CO3 (65 mL, 1 M, 65 mmol). The reaction mixture was heated at 80° C. overnight. The reaction mixture was diluted with ethyl acetate (100 ml) and washed with water (100 mL). The organic layer was concentrated under reduced pressure and the crude product was recrystallized from hexanes/ethyl acetate to afford 3-[4-(methyloxy)-3-nitrophenyl]pyridine (1.5 g, 76%). ESIMS (M+H)+=231.

Workup

  1. customNitrogen was bubbled through dioxane (100 mL)
  2. washwashed with water (100 mL)
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe crude product was recrystallized from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-d6df51ce331e49ab927f7c9469a85714
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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