Bromine → 6-Bromo-n-(5-bromo-2-thiazolyl)pyridin-2-amine

HRID 1822822Notes

Reaction equation

HRID 1822822 reaction equation
[Br:1]Br.[Br:3][C:4]1[N:9]=[C:8]([NH:10][C:11]2[S:12][CH:13]=[CH:14][N:15]=2)[CH:7]=[CH:6][CH:5]=1>C(O)(=O)C.S([O-])(O)(=O)=O.[K+]>[Br:3][C:4]1[N:9]=[C:8]([NH:10][C:11]2[S:12][C:13]([Br:1])=[CH:14][N:15]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 221704016-Bromo-N-(2-thiazolyl)pyridin-2-amine

Product 1

HCID 221704246-Bromo-n-(5-bromo-2-thiazolyl)pyridin-2-amineYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 516920Potassium bisulfateSolvent

Procedure

A solution of bromine (1.1 mL, 20.9 mmol) in acetic acid (15 mL) was added dropwise to a solution of 2-[(6-bromo-2-pyridinyl)amino]thiazole (2.68 g, 10.46 mmol) in acetic acid (23 mL) at 40° C. After addition, the mixture was stirred at rt. for 3 h. The mixture was diluted with aqueous potassium hydrogen sulfate solution (60 mL) at 0° C. and stirred for several min. The precipitated solid was filtered, washed several times with water and dried in vacuo over P2O5 to obtain the titled compound (3.28 g, 94%) as an off-white solid.

Workup

  1. additionAfter addition
  2. stirringstirred for several min
  3. filtrationThe precipitated solid was filtered
  4. washwashed several times with water
  5. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-b6d0013dc6e549008a1c794ee25b4891
Source dataset
uspto-grants-2006_05
Patent number
US07037926B2

Reaction notes

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