Potassium Carbonate → HCID 66683402, compound

HRID 1964522Notes

Reaction equation

HRID 1964522 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([O:19][C@@H:20]([CH3:24])[CH2:21][O:22][CH3:23])[CH:3]=1.[C:25]([O:29][C:30]([N:32]1[CH:36]=[CH:35][CH:34]=[C:33]1B(O)O)=[O:31])([CH3:28])([CH3:27])[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:23][O:22][CH2:21][C@H:20]([CH3:24])[O:19][C:4]1[CH:3]=[C:2]([C:33]2[N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH:36]=[CH:35][CH:34]=2)[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:5]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 66681070HCID 66681070, compound

Product 1

HCID 66683402HCID 66683402, compoundYield 94.3%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromo-3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzene (2.38 g, 5.73 mmol) synthesized in Example (13a) and 1-(t-butoxycarbonyl)pyrrole-2-boronic acid (1.45 g, 6.87 mmol) were dissolved in a mixed solvent of 1,2-dimethoxyethane (50 mL) and water (6 mL), and palladium (II) acetate (40 mg, 0.178 mmol), triphenylphosphine (180 mg, 0.686 mmol) and potassium carbonate (2.38 g, 17.2 mmol) was added, followed by stirring at 90° C. for 18 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (30 mL) and ethyl acetate (50 mL) were added, and the solution was separated. The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-40%) to afford the desired compound (2.71 g, yield 94%) as a brown oil.

Workup

  1. additionwas added
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solution was separated
  4. washThe organic layer was washed with saturated brine
  5. dry with materialsubsequently dried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified
  8. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-40%)

Sources & evidence

ORD record
ord-eb1bf0eba96e40a79eac7d0b312b5ae9
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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