Phosphorus oxychloride → 7-Chloro-3-methylthieno(3,2-b)pyridine
Reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[C:11]2=[N:12][CH:13]=[CH:14][C:15](O)=[C:10]2[S:9][CH:8]=1>ClCCCl>[Cl:3][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[C:7]([CH3:6])=[CH:8][S:9][C:10]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Phosphorous oxychloride (2.2 mL, 24 mmol) in 1,2-dichloroethane (12 mL) was charged with 3-methylthieno[3,2-b]pyridin-7-ol (2.0 g, 12 mmol). The reaction stirred overnight at reflux under nitrogen. The mixture was the cooled and concentrated. Saturated NaHCO3 solution was carefully added to neutralize the residue. The biphasic mixture was extracted with dichloromethane, dried, and concentrated. Flash chromatography (15% EtOAc/hexanes) gave the title compound (1.23 g, 55%).
Workup
- temperatureat reflux under nitrogen
- temperaturecooled
- concentrationconcentrated
- additionSaturated NaHCO3 solution was carefully added
- extractionThe biphasic mixture was extracted with dichloromethane
- customdried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7177100b147b459db6fb664eae1a6917
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354540B2
Reaction notes
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