Potassium Carbonate → HCID 68278789, compound

HRID 1506920Notes

Reaction equation

HRID 1506920 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[S:12][C:13](Br)=[C:14]([CH3:21])[C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:23]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[C:1]1([S:7]([NH:10][C:11]2[S:12][C:13]([C:25]3[CH:26]=[CH:27][O:23][CH:24]=3)=[C:14]([CH3:21])[C:15]=2[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734358Furan-3-boronic acidHCID 68278682HCID 68278682, compound2×

Product 1

HCID 68278789HCID 68278789, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of ethyl 2-benzenesulphonylamino-5-bromo-4-methylthiophene-3-carboxylate (Intermediate 34, 0.134 g), 3-furan boronic acid (0.056 g) and potassium carbonate (0.114 g) in dioxane (1.3 ml) and water (0.33 ml) was degassed and placed under nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.019 g) was added and the mixture was heated in the microwave at 150° C. for 15 minutes. The solvent was removed and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane (0-20%) to give ethyl 2-benzenesulphonylamino-5-(furan-3-yl)-4-methyl-thiophene-3-carboxylate (0.047 g) as a white solid.

Workup

  1. customwas degassed
  2. additionTetrakis(triphenylphosphine)palladium(0) (0.019 g) was added
  3. customThe solvent was removed
  4. customthe residue was purified by chromatography on silica
  5. washeluting with a mixture of ethyl acetate and cyclohexane (0-20%)

Sources & evidence

ORD record
ord-0ffacec7a9d443f6bdd8efc79828371a
Source dataset
uspto-grants-2015_12
Patent number
US09221787B2

Reaction notes

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