p-Bromochlorobenzene → Ethyl 5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)furan-2-carboxylate

HRID 1053314Notes

Reaction equation

HRID 1053314 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.C([O-])(=O)C.[K+].[S:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:28]=[CH:27][O:26][C:25]=2[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:20][CH:19]=1)(=[O:17])(=[O:16])[NH2:15]>CC(N(C)C)=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:27]2[O:26][C:25]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:24]([C:21]3[CH:20]=[CH:19][C:18]([S:14](=[O:16])(=[O:17])[NH2:15])=[CH:23][CH:22]=3)[CH:28]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 517044Potassium AcetateHCID 68285772Ethyl 3-(4-sulfamoylphenyl)furan-2-carboxylate

Product 1

HCID 60169459Ethyl 5-(4-chlorophenyl)-3-(4-sulfamoylphenyl)furan-2-carboxylateYield 9.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

1-Bromo-4-chlorobenzene (0.214 g, 1.11 mmol) and potassium acetate (0.199 g, 2.03 mmol) were added to a solution of ethyl 3-(4-sulfamoylphenyl)furan-2-carboxylate (60a, 0.3 g, 1.01 mmol) in dimethyl acetamide (5 ml) at 25° C. in a tube. A nitrogen gas was bubbled through the reaction mixture for 15 minutes. To the reaction mixture was then added palladium (II) acetate (0.023 gm, 0.102 mmol) under nitrogen atmosphere and the tube was sealed. The reaction mixture was then heated at 150° C. for 20 hr with stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and concentrated under reduced pressure. The residue so obtained was dissolved in ethyl acetate (30 ml). The solution so obtained was then washed with water (2×10 ml), dried over sodium sulphate and concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 50% ethyl acetate in hexanes as an eluent to obtain the title compound (0.040 gm, 9.70%).

Workup

  1. customA nitrogen gas was bubbled through the reaction mixture for 15 minutes
  2. temperatureThe reaction mixture was then cooled to 25° C.
  3. concentrationconcentrated under reduced pressure
  4. customThe residue so obtained
  5. customThe solution so obtained
  6. washwas then washed with water (2×10 ml)
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain a crude product, which
  10. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-d4ab7aa4fc044a5e96c11387f6c51dbb
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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