Potassium Carbonate → HCID 69111905, compound

HRID 2221139Notes

Reaction equation

HRID 2221139 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([CH2:11][N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[CH:7][C:6]=2[CH:5]=[C:4]([Cl:23])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCOCC1.O>[Cl:23][C:4]1[CH:3]=[C:2]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:10]2[O:9][C:8]([CH2:11][N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[CH:7][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 69113020HCID 69113020, compound

Product 1

HCID 69111905HCID 69111905, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of the 2-[(7-bromo-5-chloro-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione (0.500 g, 1.28 mmol), dichlorobis(tro-o-tolylphosphine)palladium(II) (0.101 g, 0.128 mmol), and potassium carbonate (0.531 g, 3.84 mmol) in dioxane (20 mL) and water (1 mL) heated to 90° C. was added phenylboronic acid (0.390 g, 3.20 mmol) and the reaction allowed to stir for 1 h. The reaction was cooled to room temperature, filtered (celite), and the solvent removed in vacuo to provide a crude residue. Purification by flash column chromatography (silica, ethyl acetate:hexanes 1:4) gave 0.422 g (85%) of 2-[(5-chloro-7-phenyl-1-benzofuran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione as a white solid. mp 163-166° C.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered (celite)
  3. customthe solvent removed in vacuo
  4. customto provide a crude residue
  5. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 1:4)

Sources & evidence

ORD record
ord-fca99eab524e4b108195c60058dfe378
Source dataset
uspto-grants-2008_05
Patent number
US07368477B2

Reaction notes

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