Potassium Carbonate → HCID 67268273, compound

HRID 598173Notes

Reaction equation

HRID 598173 reaction equation
FC(F)(F)S(O[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:16])[CH2:10][CH2:11]2)(=O)=O.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1B(O)O.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:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[C:9](=[O:16])[CH2:10][CH2:11]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 57164514HCID 57164514, compound

Product 1

HCID 67268273HCID 67268273, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A solution containing 3-oxo-2,3-dihydro-1H-inden-4-yl trifluoromethanesulfonate (0.666 g, 2.38 mmol), 2,4-dichlorobenzeneboronic acid (0.907 g, 4.75 mmol), and potassium carbonate (0.657 g, 4.75 mmol) in toluene (10 mL) stirred at room temperature for 15 minutes. Pd(PPh3)4 (1.37 g, 1.19 mmol) was added and the mixture was stirred at 90° C. for 2 hours. The catalyst was removed by filtration and concentrated. Flash chromatography gave the desired product as a brown solid (0.572 g, 87%).

Workup

  1. stirringthe mixture was stirred at 90° C. for 2 hours
  2. customThe catalyst was removed by filtration
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cfe1fc3ed1104c54a13600f657649400
Source dataset
uspto-grants-2011_03
Patent number
US07897607B2

Reaction notes

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