Phosphorus oxychloride → 7-Chloro-2-phenylthieno[3,2-b]pyridine-6-carbonitrile

HRID 1611501Notes

Reaction equation

HRID 1611501 reaction equation
O=[C:2]1[C:7]([C:8]#[N:9])=[CH:6][NH:5][C:4]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:12][C:3]1=2.P(Cl)(Cl)([Cl:21])=O>CCCCCC>[Cl:21][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[S:12][C:3]=12

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22256667HCID 22256667, compound

Product 1

HCID 222566757-Chloro-2-phenylthieno[3,2-b]pyridine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 7-oxo-2-phenyl-4,7-dihydrothieno[3,2-b]pyridine-6-carbonitrile (878 mg, 3.48 mmol) and 10 mL of phosphorous oxychloride is heated at reflux for 1 hour. The reaction mixture is cooled to room temperature and hexane is added. The solids are collected by filtration and stirred with saturated aqueous sodium bicarbonate. The solids are collected by filtration washing with water, ethyl acetate and methanol to provide 751 mg of 7-chloro-2-phenylthieno[3,2-b]pyridine-6-carbonitrile that is not purified.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe solids are collected by filtration
  4. filtrationThe solids are collected by filtration
  5. washwashing with water, ethyl acetate and methanol

Sources & evidence

ORD record
ord-7097db4301734b9c865aa3e952ab17ad
Source dataset
uspto-grants-2006_01
Patent number
US06987116B2

Reaction notes

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