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

HRID 226061Notes

Reaction equation

HRID 226061 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C(=O)(O)[O-].[Na+].OP([O-])([O-])=O.[K+].[K+].[O-]S([O-])(=O)=O.[Mg+2].[Br:28]Br>O.C(Cl)(Cl)Cl>[Br:28][C:3]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[S:1][CH:2]=1

Participants

8

Reactant 5

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24408Bromine2×HCID 24450Potassium Phosphate, DibasicHCID 516892Sodium BicarbonateHCID 12210218Thienopyridine

Product 1

HCID 132204283-Bromothieno[3,2-b]pyridineYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

3.45 g of Thieno[3,2-b]pyridine (25.6 mmol), 2.15 g of sodium bicarbonate (25.6 mmol), 6.69 g of K2HPO4 (38.4 mmol) and 4.01 g of MgSO4 (33.3 mmol) are placed in the flask with 60 ml of CHCl3. The mixture is stirred under reflux and 1.57 ml of Br2 (30.7 mmol) is added slowly. The reaction mixture is stirred under reflux overnight. Additional 0.7 ml of bromine is added and stirred under reflux for 4 h and cooled to room temperature. Water is added and extracted with CHCl3. The separated CHCl3 is washed by sat. Na2S2O3 and sat. NaCl and dried over Na2SO4 and evaporated. The title compound is recrystallized from Hexane/CH2Cl2. 3.94 g, Yield 72%. mass spectrum (m/e): 215 (M+1); 1H-NMR (CDCl3): 8.86 (d, 1H, J=5.2 Hz), 8.24 (d, 1H, J=8.2 Hz), 7.82 (s, 1H), 7.38 (dd, 1H, J=8.2 Hz, 5.2 Hz) ppm.

Workup

  1. temperatureunder reflux
  2. stirringThe reaction mixture is stirred
  3. temperatureunder reflux overnight
  4. stirringstirred
  5. temperatureunder reflux for 4 h
  6. extractionextracted with CHCl3
  7. washThe separated CHCl3 is washed by sat. Na2S2O3 and sat. NaCl
  8. dry with materialdried over Na2SO4
  9. customevaporated
  10. customThe title compound is recrystallized from Hexane/CH2Cl2

Sources & evidence

ORD record
ord-b718903e6dc44b728b56ca27d9de17c3
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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