Sodium Carbonate → 7-Bromo-4-chloro-2-phenylthieno[3,2-c]pyridine

HRID 1868325Notes

Reaction equation

HRID 1868325 reaction equation
[Br:1][C:2]1[C:3]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][C:4]=2[C:5](=O)[NH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].P(Cl)(Cl)([Cl:26])=O>>[Br:1][C:2]1[C:3]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:9][C:4]=2[C:5]([Cl:26])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 184465837-Bromo-2-phenylthieno[3,2-c]pyridin-4(5H)-one

Product 1

HCID 184465857-Bromo-4-chloro-2-phenylthieno[3,2-c]pyridine

Procedure

A mixture of 7-bromo-2-phenyl-5H-thieno[3,2-c]pyridin-4-one 3 (2.28 g, 7.5 mmol) in phosphorus oxychloride (27 mL) was heated at reflux for 21 h. The reaction mixture was basified to pH 5-6 by the addition of saturated aqueous sodium carbonate and extracted with dichloromethane (1×). The organic layer was dried over Na2SO4, filtered, and the filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 97:3) to give 95.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 21 h
  3. extractionextracted with dichloromethane (1×)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate was purified by silica gel column chromatography (eluent: hexane:EtOAc, 97:3)

Sources & evidence

ORD record
ord-b610453387d640f2b8c1d5302495c3ef
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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