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

HRID 1916735Notes

Reaction equation

HRID 1916735 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
  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-f1459f5f2dd94fb7962303a1d93132c3
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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