Ethanol → HCID 68285874, compound

HRID 1053269Notes

Reaction equation

HRID 1053269 reaction equation
Br[C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[S:4][C:3]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(O)C.[S:22]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)(=[O:25])(=[O:24])[NH2:23].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>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[S:4][C:3]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:2]([C:29]3[CH:30]=[CH:31][C:26]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:27][CH:28]=3)[CH:6]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 223919774-(Aminosulphonyl)benzeneboronic acidHCID 68285842HCID 68285842, compound2×

Product 1

HCID 68285874HCID 68285874, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of Ethyl 3-bromo-5-(4-chlorophenyl)thiophene-2-carboxylate (compound 33a, 1.45 g, 4.19 mmol) in a mixture of toluene: ethanol (10:40 ml) was added (4-sulfamoylphenyl)boronic acid (0.84 g, 4.19 mmol) and potassium carbonate (1.16 g, 8.39 mmol) at 25° C. Nitrogen gas was bubbled through the reaction mixture for 15 minutes. To the reaction mixture was then added tetrakis(triphenylphosphine)palladium(0) (0.24 g, 0.20 mmol) under nitrogen atmosphere and the reaction mixture was heated at about 95 to about 100° C. for 16 hr under stirring. The progress of the reaction was monitored by TLC. The reaction mixture was then cooled to 25° C. and filtered through celite, the celite cake was washed with Ethanol (2×25 ml). The filtrate so obtained was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography over silica gel (100-200 mesh) using 50% ethyl acetate in hexanes as an eluent to obtain the title compound (1.35 g, 76.27%).

Workup

  1. customNitrogen gas was bubbled through the reaction mixture for 15 minutes
  2. filtrationfiltered through celite
  3. washthe celite cake was washed with Ethanol (2×25 ml)
  4. customThe filtrate so obtained
  5. concentrationwas concentrated under reduced pressure
  6. customto obtain a crude product, which
  7. customwas then purified by column chromatography over silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-33036492e17c4f0fb3a6ead88658fe0c
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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