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

HRID 1294750Notes

Reaction equation

HRID 1294750 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-7e818fe299174c34a75eb6d28740d3d9
Source dataset
uspto-grants-2007_07
Patent number
US07241781B2

Reaction notes

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