Sulfuric acid magnesium salt (1:1) → 3-Bromothieno[2,3-b]pyridine

HRID 1890538Notes

Reaction equation

HRID 1890538 reaction equation
[Br:1]Br.[S:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1.P([O-])([O-])(O)=O.[K+].[K+].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)(Cl)Cl>[Br:1][C:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[S:3][CH:4]=1

Participants

7

Reactant 5

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24408BromineHCID 24450Potassium Phosphate, DibasicHCID 289928Thieno(2,3-b)pyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 2899263-Bromothieno[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (2.08 g, 13 mmol) was dropwise added to a mixture of thieno[2,3-b]pyridine (J-2) (1.35 g, 10 mmol), dipotassium monohydrogen orthophosphate (940 mg, 5.4 mmol), sodium bicarbonate (840 mg 10 mmol), and magnesium sulfate (2.0 g, 16.7 mmol) in chloroform (40 mL) which has been stirred at reflux for 16 h, the resulting mixture was stirred under reflux for 24 h, then filtered and washed with DCM. The filtrate was concentrated, and purified by chromatography. MS (m/z): 214 (M+1)+.

Workup

  1. temperatureat reflux for 16 h
  2. stirringthe resulting mixture was stirred
  3. temperatureunder reflux for 24 h
  4. filtrationfiltered
  5. washwashed with DCM
  6. concentrationThe filtrate was concentrated
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-86b915d2acef49309534f2db9e20235f
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

Loading…