Pyridine → tert-Butyl 3-bromo-6-chloropyridine-2-carboxylate

HRID 1778819Notes

Reaction equation

HRID 1778819 reaction equation
S(Cl)(C1C=[CH:9][C:7]([CH3:8])=[CH:6]C=1)(=O)=O.[Cl:12][C:13]1(C(O)=O)[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][NH:14]1.N1C=CC=CC=1.[C:29]([O-:32])(O)=[O:30].[Na+]>C(O)(C)(C)C>[Br:19][C:16]1[C:15]([C:29]([O:32][C:7]([CH3:9])([CH3:8])[CH3:6])=[O:30])=[N:14][C:13]([Cl:12])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 86644327HCID 86644327, compound

Product 1

HCID 59447676tert-Butyl 3-bromo-6-chloropyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Tosyl chloride (7.7 g) was added to a solution of 2-chloro-5-bromo picolinic acid (4 g) and pyridine (9.2 mL) in t-butanol (33 mL) at 0° C. The reaction was then stirred at room temperature for 12 hours. NaHCO3 (aqueous, saturated) was then added and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with brine and dried over Na2SO4. Filtration and evaporation of the organic solvent provided the title compound which was used in the next step without further purification.

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation of the organic solvent

Sources & evidence

ORD record
ord-6c8ec89075524b29a0910125715a9477
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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