Potassium Carbonate → HCID 68285619, compound

HRID 1053301Notes

Reaction equation

HRID 1053301 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11](=O)([O-])[O-].[K+].[K+].Br[C:18]1[S:22][C:21]([C:23]([O:25][CH3:26])=[O:24])=[C:20]([C:27]2[CH:32]=[CH:31][C:30]([S:33](=[O:36])(=[O:35])[NH2:34])=[C:29]([CH3:37])[CH:28]=2)[C:19]=1[CH3:38]>C1(C)C=CC=CC=1.C(O)C.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:1][C:2]1[CH:7]=[CH:6][C:5]([C:18]2[S:22][C:21]([C:23]([O:25][CH2:26][CH3:11])=[O:24])=[C:20]([C:27]3[CH:32]=[CH:31][C:30]([S:33](=[O:36])(=[O:35])[NH2:34])=[C:29]([CH3:37])[CH:28]=3)[C:19]=2[CH3:38])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 68285248HCID 68285248, compound

Product 1

HCID 68285619HCID 68285619, compoundYield 76.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

(4-chlorophenyl)boronic acid [0.29 g, 1.85 mmol] and potassium carbonate (0.43 g, 3.09 mmol) were added to a solution of methyl 5-bromo-4-methyl-3-(3-methyl-4-sulfamoylphenyl)thiophene-2-carboxylate (41b, 0.62 g, 1.54 mmol) in a mixture of 5 ml of toluene and 20 ml ethanol at 25° C. A nitrogen gas was bubbled through reaction mixture for 15 minutes. To the reaction mixture was then added tetrakis(triphenylphosphine)palladium(0) (0.09 g, 0.08 mmol) under nitrogen atmosphere and the reaction mixture was heated at a temperature between about 95° C. to 100° C. for 3 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 ethyl acetate (20 ml). The combined filtrate was then concentrated under reduced pressure to obtain a crude product, which was then purified by flash column chromatography using 30% ethyl acetate in hexanes as an eluent to obtain the title compound (0.53 g, 76.8%).

Workup

  1. customA nitrogen gas was bubbled through reaction mixture for 15 minutes
  2. filtrationfiltered through celite
  3. washThe celite cake was washed with ethyl acetate (20 ml)
  4. concentrationThe combined filtrate was then concentrated under reduced pressure
  5. customto obtain a crude product, which
  6. customwas then purified by flash column chromatography

Sources & evidence

ORD record
ord-fdc4b6f5215d4167a2b4ff3fb636563d
Source dataset
uspto-grants-2016_07
Patent number
US09393247B2

Reaction notes

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