Hydrochloric Acid → 2-(4-Chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one

HRID 2384885Notes

Reaction equation

HRID 2384885 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:36][C:11]3[C:12](=[O:35])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][Si](C(C)C)(C(C)C)C(C)C)=[C:18]([O:33][CH3:34])[CH:17]=4)[CH2:14][CH2:15][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:36][C:11]3[C:12](=[O:35])[N:13]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:33][CH3:34])[CH:17]=4)[CH2:14][CH2:15][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 68950353HCID 68950353, compound

Product 1

HCID 689499992-(4-Chloro-phenyl)-6-(4-hydroxy-3-methoxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-oneYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 2-(4-chloro-phenyl)-6-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-5,6-dihydro-4H-thieno[2,3-c]pyridin-7-one (1.68 g, 3.1 mmol) in THF (20 mL) and add 1.0 M solution of tetrabutyl ammonium fluoride in THF (3.1 mL, 3.1 mmol). Stir at RT for 1 h. Slowly add 1N HCl until pH is approximately 1. A precipitate begins to form. Allow to sit at RT for 2-3 h. Filter the resulting solid to yield 850 mg (71% yield) of the desired product. MS/ES m/z (35Cl) 386.0 [M+H]+.

Workup

  1. customto form
  2. waitAllow to sit at RT for 2-3 h
  3. filtrationFilter the resulting solid

Sources & evidence

ORD record
ord-c18935d7b09e4e889a980a1004605eeb
Source dataset
uspto-grants-2012_09
Patent number
US08263772B2

Reaction notes

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