Dimethylformamide → 7-Chlorothieno[3,2-b]pyridine

HRID 888046Notes

Reaction equation

HRID 888046 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][C:8]=2O)[CH:3]=[CH:2]1.S(Cl)([Cl:13])=O.CN(C=O)C>C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[Cl:13][C:8]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:3]=[CH:2][S:1][C:9]=12

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 5074765Thieno[3,2-b]pyridin-7-ol

Product 1

HCID 112752517-Chlorothieno[3,2-b]pyridineYield 50%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

Thieno[3,2,b]pyridin-7-ol (200 mg; 1.32 mmol) was added to thionyl chloride (1.57 g; 13.2 mmol), followed by a drop of DMF. The solution was stirred at 80° C. for 4 hours. The cooled solution was diluted with ethyl acetate and neutralised to pH 7 with a saturated solution of sodium hydrogen carbonate (25 ml). The organic layer was washed with brine, dried and concentrated to yield the title compound (112 mg; 50%); Mass Spectrum: M+H+ 170.

Workup

  1. washThe organic layer was washed with brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8ed9d1dd5c2a4b4db94d2db0d727b331
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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