Acetic Acid → 4-(5-Bromopyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

HRID 2216039Notes

Reaction equation

HRID 2216039 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([N+]([O-])=O)=[C:8]([S:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4].[CH3:23][S-:24].[Na+].C(O)(=O)C>>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([S:24][CH3:23])=[C:8]([S:10]([C:13]2[CH:14]=[N:15][CH:16]=[C:17]([Br:19])[CH:18]=2)(=[O:12])=[O:11])[CH:9]=1)=[O:4]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4378561Sodium methanethiolateHCID 695864994-(5-Bromo-pyridine-3-sulfonyl)-5-nitro-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 210571784-(5-Bromopyridine-3-sulfonyl)-5-methylsulfanyl-thiophene-2-carboxylic acid methyl ester

Procedure

The procedure described in Example 27: step a was followed using 4-(5-Bromo-pyridine-3-sulfonyl)-5-nitro-thiophene-2-carboxylic acid methyl ester (151 mg, 0.37 mmol, Example 127: step c) and sodium thiomethoxide (1.0 M in EtOH, 26.3 mg, 0.37 mmol). The reaction was quenched with acetic acid (21 uL, 0.37 mol) and the solvents were removed in vacuo. The residue was then dissolved into EtOAc and washed with saturated NaHCO3 and brine solutions. The organic layer was dried (Na2SO4) and removal of the solvents in vacuo was followed by purification by flash column chromatography SiO2 (30% EtOAc in hexanes) to yield the title compound. ESI-MS (m/z): Calcd. for C12H10BrNO4S3: 407.9 (M+1) found: 408.1.

Workup

  1. customthe solvents were removed in vacuo
  2. dissolutionThe residue was then dissolved into EtOAc
  3. washwashed with saturated NaHCO3 and brine solutions
  4. customThe organic layer was dried
  5. custom(Na2SO4) and removal of the solvents in vacuo
  6. customwas followed by purification by flash column chromatography SiO2 (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4c660d7b4540422b8c2adc06d39407d3
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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