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

HRID 1268872Notes

Reaction equation

HRID 1268872 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. 1H NMR (400 MHz, CDCl3) δ: 7.41–7.52 (m, 3H), 7.72–7.78 (m, 3H), 8.28 (s, 1H). MS (EI) m/z (M+H+) 324.

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-3ab4d4f39ef749538d8cd64226363089
Source dataset
uspto-grants-2007_04
Patent number
US07199119B2

Reaction notes

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