Potassium Carbonate → HCID 66683297, compound

HRID 1964513Notes

Reaction equation

HRID 1964513 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]([OH:10])[CH2:8][OH:9])[N:6]=1.[C:11]([O:15][C:16]([N:18]1[CH:22]=[CH:21][CH:20]=[C:19]1B(O)O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[OH:10][CH:7]([C:5]1[N:6]=[C:2]([C:19]2[N:18]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])[CH:22]=[CH:21][CH:20]=2)[S:3][CH:4]=1)[CH2:8][OH:9]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 66681631HCID 66681631, compound

Product 1

HCID 66683297HCID 66683297, compoundYield 59%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

1-(2-Bromo-1,3-thiazol-4-yl)ethane-1,2-diol (1.10 g, 4.91 mmol) synthesized in Example (9b) and commercially available 1-(t-butoxycarbonyl)pyrrole-2-boronic acid (1.55 g, 7.35 mmol) were dissolved in 1,2-dimethoxyethane (40 mL), and palladium (II) acetate (55.0 mg, 0.245 mmol), triphenylphosphine (260 mg, 0.991 mmol) and an aqueous potassium carbonate solution (3M, 4.9 mL, 14.7 mmol) were added, followed by stirring at 100° C. for 14 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (30 mL) and ethyl acetate (40 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=50%-100%) to afford the desired compound (868 mg, yield 59%) as a brown oil.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solution was separated
  3. washThe organic layer was washed with saturated brine
  4. dry with materialsubsequently dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified
  7. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=50%-100%)

Sources & evidence

ORD record
ord-f3ecf17e3a594e40b65d74b0bf676c3f
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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