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

HRID 49141Notes

Reaction equation

HRID 49141 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-41b5aa3c69284baa8eaf2ac09a2ca4fe
Source dataset
uspto-grants-2004_03
Patent number
US06706717B2

Reaction notes

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