Ethanol → Ethyl-5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylate

HRID 1053247Notes

Reaction equation

HRID 1053247 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:8]([CH3:11])[C:9]=1Br)=[O:4].[CH2:19](O)C.[NH2:22][S:23]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:2][C:3]([C:5]1[S:6][C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:8]([CH3:11])[C:9]=1[C:29]1[CH:30]=[CH:31][C:26]([S:23](=[O:25])(=[O:24])[NH2:22])=[CH:27][CH:28]=1)=[O:4])[CH3:19]

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 68285497Methyl 3-bromo-5-(4-chlorophenyl)-4-methylthiophene-2-carboxylate2×

Product 1

HCID 68285835Ethyl-5-(4-chlorophenyl)-4-methyl-3-(4-sulfamoylphenyl)thiophene-2-carboxylateYield 48%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl-3-bromo-5-(4-chlorophenyl)-4-methylthiophene-2-carboxylate (compound 1a, 2.2 g, 6.3 mmol) in a mixture of toluene: ethanol (10:30 ml) were added 4-aminosulfonylbenzene boronic acid (prepared according to the procedure given in EP 1012142, 1.28 g, 6.3 mmol) and potassium carbonate (1.76 g, 12.7 mmol) at 25° C. in a sealed tube and nitrogen gas was bubbled through the reaction mixture for 15 minutes. To this was added tetrakis(triphenylphosphine)palladium(0) (0.370 g, 0.318 mmol) under nitrogen and the reaction mixture was heated at about 95-about 100° C. for 18 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was cooled to 25° C. and filtered through celite. The filtrate was concentrated under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 40% ethyl acetate in hexanes as an eluent to obtain the title compound (1.3 g, 48%).

Workup

  1. customprepared
  2. customat 25° C.
  3. customnitrogen gas was bubbled through the reaction mixture for 15 minutes
  4. temperaturethe reaction mixture was heated at about 95-about 100° C. for 18 hr
  5. filtrationfiltered through celite
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customto obtain a crude product, which
  8. customwas purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-6c91b5b23c10491cb24586a1867da09e
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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