Triethylamine → 5-Bromo-3-chloro-N-methoxy-N-methylpicolinamide

HRID 623915Notes

Reaction equation

HRID 623915 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([C:8](O)=[O:9])=[N:6][CH:7]=1.ON1C2C=CC=CC=2N=N1.Cl.[CH3:23][NH:24][O:25][CH3:26].C(N(CC)CC)C>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([C:8]([N:24]([O:25][CH3:26])[CH3:23])=[O:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 459338155-Bromo-3-chloropyridine-2-carboxylic acid

Product 1

HCID 866981795-Bromo-3-chloro-N-methoxy-N-methylpicolinamideYield 95.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (24 mL) was dissolved 5-bromo-3-chloropyridine-2-carboxylic acid (2.36 g), 1-hydroxybenzotriazole (2.2 g) and 3-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.87 g), N,O-dimethylhydroxylamine hydrochloride (1.27 g) and triethylamine (1.95 mL) was added to the solution, and the resulting mixture was stirred at room temperature for 20 hours. Water was added to the obtained residue, extracted with ethyl acetate, and the organic layer was washed with water and then with a saturated brine. After drying the mixture over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure to obtain 5-bromo-3-chloro-N-methoxy-N-methylpyridine-2-carboxamide (2.67 g).

Workup

  1. additionwas added to the solution
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialAfter drying the mixture over anhydrous magnesium sulfate
  5. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4c13e6800b12474f8e82bf4c7de18409
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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