Phosphorus oxychloride → 7-Chloro-3-methylthieno(3,2-b)pyridine

HRID 1806173Notes

Reaction equation

HRID 1806173 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]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178431852HCID 178431852, compound

Product 1

HCID 574158647-Chloro-3-methylthieno(3,2-b)pyridineYield 55.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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

  1. temperatureat reflux under nitrogen
  2. temperaturecooled
  3. concentrationconcentrated
  4. additionSaturated NaHCO3 solution was carefully added
  5. extractionThe biphasic mixture was extracted with dichloromethane
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7177100b147b459db6fb664eae1a6917
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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