Methyl Thioglycolate → 3-(1-Benzoylpiperidin-4-yl)-6-fluorobenzo[b]thiophene-2-carboxylic acid

HRID 1784721Notes

Reaction equation

HRID 1784721 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15](=O)[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2F)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25]([O:29]C)(=[O:28])[CH2:26][SH:27]>CN(C)C=O>[C:1]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=3[S:27][C:26]=2[C:25]([OH:29])=[O:28])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 16907Methyl ThioglycolateHCID 671173731-Benzoyl-4-(2,4-difluorobenzoyl)piperidine

Product 1

HCID 536289613-(1-Benzoylpiperidin-4-yl)-6-fluorobenzo[b]thiophene-2-carboxylic acidYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-benzoyl-4-(2,4-difluorobenzoyl)piperidine (40 g, 120 mmol), methyl thioglycolate (12 mL, 130 mmol) in dimethylformamide (500 mL) was stirred at room temperatute for 12 h. The solvent was evaporated off in vacuo and the residue treated with water and ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography eluting hexane/ethyl acetate to give 3-(1-benzoylpiperidin-4-yl)-6-fluorobenzo[b]thiophene-2-carboxylic acid (11.8 g, 26%) as an oil.

Workup

  1. customThe solvent was evaporated off in vacuo
  2. additionthe residue treated with water and ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography
  6. washeluting hexane/ethyl acetate

Sources & evidence

ORD record
ord-b25fa8f7b0bf4611ae0ad75b5ca0c225
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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