Potassium Carbonate → HCID 50940070, compound

HRID 1643177Notes

Reaction equation

HRID 1643177 reaction equation
Br[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:7]=12.C([O-])([O-])=O.[K+].[K+].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1(C)C=CC=CC=1.CCO.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:8]2[C:7]3=[C:2]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:3]=[CH:4][CH:5]=[C:6]3[CH:10]=[CH:9]2)(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 72711738HCID 72711738, compound

Product 1

HCID 50940070HCID 50940070, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 3 (0.1 g, 0.273 mmol) in toluene (8 mL) was treated with tetrakis(triphenylphosphine) palladium (0.016 g, 0.014 mmol). An aqueous solution of K2CO3 (2 M, 1 mL) was then added, followed by a solution of phenylboronic acid (0.037 g, 0.3 mmol) in EtOH (5 mL). The resulting mixture was then refluxed for 24 h. The solvent was removed and the residue was purified by flash chromatography (EtOAc:n-hexane=2:3) to give Compound 6 (26.6 mg, 27%).

Workup

  1. temperatureThe resulting mixture was then refluxed for 24 h
  2. customThe solvent was removed
  3. customthe residue was purified by flash chromatography (EtOAc:n-hexane=2:3)

Sources & evidence

ORD record
ord-597a38797feb44d3b2669e83abc20f24
Source dataset
uspto-grants-2012_02
Patent number
US08119683B2

Reaction notes

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