Sodium Carbonate → HCID 22502594, compound

HRID 1006932Notes

Reaction equation

HRID 1006932 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[CH:18]=[CH:17][S:16][C:12]3=[CH:13][N+:14]=2[O-])=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:36]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)[CH3:37]>CS(C)=O>[CH2:36]([N:38]1[CH2:43][CH2:42][N:41]([C:13]2[N:14]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=[C:11]3[CH:18]=[CH:17][S:16][C:12]=23)[CH2:40][CH2:39]1)[CH3:37]

Participants

7

Reactant 5

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 791961-EthylpiperazineHCID 22502445HCID 22502445, compound

Product 1

HCID 22502594HCID 22502594, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-(4-Methoxyphenyl)thieno[2,3-c]pyridine-6-oxide (3.0 g) was reacted with phosphorus oxychloride (15 ml) at 100° C. for 3 hr. The reaction mixture was poured into ice-water, neutralized with sodium carbonate and extracted with ethyl acetate. The organic layer was washed with water and brine and dried. The extract was filtered through silica gel, and the column was washed with ethyl acetate. The filtrates were combined and concentrated. The resulting 7-chloro-5-(4-methoxyphenyl)thieno[2,3-c]pyridine (2.1 g) was reacted reacted in N-ethylpiperazine (5 ml) and dimethyl sulfoxide (20 ml) with potassium carbonate (5.0 g) at 100° C. for 1 day. The reaction solution was evaporated, and the resulting residue was partitioned between ethyl acetate and water and extracted with ethyl acetate. The organic layer was washed with water and dried. Then, the solvent was removed, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 0.93 g of the title compound of as a pale brown oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. filtrationThe extract was filtered through silica gel
  5. washthe column was washed with ethyl acetate
  6. concentrationconcentrated
  7. customThe resulting 7-chloro-5-(4-methoxyphenyl)thieno[2,3-c]pyridine (2.1 g) was reacted
  8. customThe reaction solution was evaporated
  9. customthe resulting residue was partitioned between ethyl acetate and water
  10. extractionextracted with ethyl acetate
  11. washThe organic layer was washed with water
  12. customdried
  13. customThen, the solvent was removed
  14. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-0d9b82fa1fd840da826e7ea827fed19d
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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