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

HRID 588649Notes

Reaction equation

HRID 588649 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-07e7286923644ef1bc001784cb5b1e73
Source dataset
uspto-grants-2016_01
Patent number
US09227963B2

Reaction notes

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