Pyridine → 5-Bromo-3-(morpholinosulfonyl)pyridin-2-amine

HRID 1952305Notes

Reaction equation

HRID 1952305 reaction equation
[NH2:1][C:2]1[C:7]([S:8](Cl)(=[O:10])=[O:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.N1C=CC=CC=1>O1CCOCC1>[Br:12][C:5]1[CH:6]=[C:7]([S:8]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8083MorpholineHCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Product 1

HCID 621482705-Bromo-3-(morpholinosulfonyl)pyridin-2-amineYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-5-bromo-3-pyridinesulfonyl chloride (0.50 g, 1.84 mmol) in anhydrous dioxane (2 mL) cooled to 5° C. was added (0.16 mL, 1.84 mmol) of morpholine followed by (0.174 mL, 2.15 mmol) of pyridine. The reaction mixture was stirred at room temperature for 2 hrs and then heated at 50° C. for 1 hour. After cooling to room temperature, a white precipitate formed which was collected by suction filtration, washing with water and petroleum ether to give the title compound as an off-white solid. (0.539 g, 91% yield). MS(ES)+ m/e 323.9 [M+H]+.

Workup

  1. temperatureheated at 50° C. for 1 hour
  2. temperatureAfter cooling to room temperature
  3. customa white precipitate formed which
  4. filtrationwas collected by suction filtration
  5. washwashing with water and petroleum ether

Sources & evidence

ORD record
ord-5e30ea7fb1244f76be8a6827aebd0340
Source dataset
uspto-grants-2013_03
Patent number
US08404837B2

Reaction notes

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