Sodium Carbonate → 5-Bromo-2-(4-chlorophenyl)pyridine

HRID 271732Notes

Reaction equation

HRID 271732 reaction equation
C([O-])([O-])=O.[Na+].[Na+].[Br:7][C:8]1[CH:9]=[CH:10][C:11](I)=[N:12][CH:13]=1.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](OB(O)O)=[CH:18][CH:17]=1>O1CCOCC1.CO>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)=[N:12][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 5936905-Bromo-2-iodopyridineHCID 17810664p-Chlorophenylboric acid

Product 1

HCID 131283835-Bromo-2-(4-chlorophenyl)pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Under an N2 atmosphere 11 mL 2 M Na2CO3 solution and 240 mg (0.21 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 3.00 g (10.6 mmol) 5-bromo-2-iodo-pyridine and 3.37 g (21.1 mmol) 4-chlorophenyl-boric acid in 60 mL 1,4-dioxane and 15 mL MeOH and the reaction mixture is heated to 110° C. for 3 h. The mixture is evaporated down i.vac., the residue is combined with 50 mL water, 10 mL 3% NH3 solution and 150 mL EtOAc, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc).

Workup

  1. customThe mixture is evaporated down i.vac
  2. customthe organic phase is separated off
  3. dry with materialdried over Na2SO4
  4. customis purified by chromatography (silica gel, cyc)

Sources & evidence

ORD record
ord-a4275179605f4b9aa9ffe8baccbc9b31
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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