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

HRID 723086Notes

Reaction equation

HRID 723086 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. customremoval of the solvents in vacuo
  5. customwas followed by purification by flash column chromatography SiO2 (30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5ca28426b73948e48e7cac65f1429030
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Reaction notes

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