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

HRID 226069

Reaction equation

HRID 226069 reaction equation
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]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>[Br:28][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:1][CH:2]=1

Participants

8

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]pyridineYield 48.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2.30 g of Thieno[2,3-b]pyridine (17 mmol), 1.43 g of NaHCO3 (17 mmol), 4.44 g of K2HPO4 (25.5 mmol) and 2.66 g of MgSO4 (22.1 mmol) are placed into the flask with 80 ml of dichloromethane. The reaction mixture is stirred under reflux. 1.05 ml of bromine (20.4 mmol) is added slowly to the mixture and is stirred overnight. CH2Cl2 and water are added to the cooled reaction mixture and separated. The CH2Cl2 layer is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane: AcOEt=3:1) to give 1.76 g of the title compound. Yield 48%. mass spectrum (m/e): 215 (M+1); 1H-NMR (CDCl3): 8.67 (m, 1H), 8.13 (m, 1H), 7.59 (s, 1H), 7.45 (m, 1H) ppm.

Workup

  1. temperatureunder reflux
  2. stirringis stirred overnight
  3. customseparated
  4. dry with materialThe CH2Cl2 layer is dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-137de9ad09d94fd7bf2c4d32b1346a4c
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Linked notes

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