Sodium Carbonate → 5-Bromo-2-chloro-4-(2-chloro-phenyl)-pyridine

HRID 1835329Notes

Reaction equation

HRID 1835329 reaction equation
[Br:1][C:2]1[C:3](I)=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[Br:1][C:2]1[C:3]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[Cl:10])=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343222-Chlorophenylboronic acidHCID 218651405-Bromo-2-chloro-4-iodopyridine

Product 1

HCID 235028315-Bromo-2-chloro-4-(2-chloro-phenyl)-pyridineYield 75.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 10.8 g (33.9 mmol) 5-bromo-2-chloro-4-iodo-pyridine, 5.84 g (37.3 mmol) 2-chlorophenylboronic acid, 200 ml dimethoxyethane and 50 ml of a 2 M aqueous solution of sodium carbonate was deoxygenated by three freeze-thaw cycles. After addition of 381 mg (1.70 mmol) palladium(II) acetate and 917 mg (3.39 mmol) triphenylphosphine the reaction mixture was stirred at 90° C. for 4 h. Cooling to room temperature was followed by dilution with water and extraction with two portions of tert-butyl methyl ether. The combined organic extracts were washed with brine, dried with magnesium sulfate and concentrated. Column chromatography afforded 7.74 g (75%) of the title compound as a white solid.

Workup

  1. customwas deoxygenated by three freeze-thaw cycles
  2. temperatureCooling to room temperature
  3. extractionwas followed by dilution with water and extraction with two portions of tert-butyl methyl ether
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6bff178f0b344758b64c8531de2dea4
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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