Potassium Carbonate → t-Butyl 2-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylate

HRID 909420Notes

Reaction equation

HRID 909420 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:17]1[S:18][CH:19]=[CH:20][N:21]=1.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>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[C:9]1[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 764302-BromothiazoleHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid

Product 1

HCID 66681244t-Butyl 2-(1,3-thiazol-2-yl)-1H-pyrrole-1-carboxylateYield 56.2%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
90 °C

Procedure

Commercially available 1-(t-butoxycarbonyl)pyrrole-2-boronic acid (10.06 g, 47.7 mmol) was dissolved in a mixed solvent of 1,2-dimethoxyethane (150 mL) and water (25 mL), and 2-bromothiazole (4.40 mL, 48.8 mmol), palladium (II) acetate (535 mg, 2.38 mmol), triphenylphosphine (2.50 g, 9.53 mmol) and potassium carbonate (19.50 g, 141 mmol) were added, followed by stirring at 90° C. for 16 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (300 mL) and ethyl acetate (400 mL) were added, and the solution was separated. The organic layer was washed with saturated brine, and subsequently dried over sodium 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=0%-20%) to afford the desired compound (6.71 g, yield 56%) as a pale yellow oil.

Workup

  1. additionwere 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 sodium 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=0%-20%)

Sources & evidence

ORD record
ord-3cb8d5f397aa42dca38df76a45ce472c
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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