Potassium Carbonate → HCID 66681296, compound

HRID 1964517Notes

Reaction equation

HRID 1964517 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH:23]=[CH:22][CH:21]=[C:20]1B(O)O)=[O:18])([CH3:15])([CH3:14])[CH3:13].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>[C:12]([O:16][C:17]([N:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 13349623Methyl 6-bromopyridine-3-carboxylate

Product 1

HCID 66681296HCID 66681296, compoundYield 92%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
100 °C

Procedure

Commercially available methyl 6-bromonicotinate (650 mg, 3.01 mmol) and commercially available 1-(t-butoxycarbonyl)pyrrole-2-boronic acid (960 mg, 4.34 mmol) were dissolved in 1,2-dimethoxyethane (30 mL), and palladium (II) acetate (34.0 mg, 0.151 mmol), triphenylphosphine (158 mg, 0.602 mol) and an aqueous potassium carbonate solution (2M, 4.5 mL, 9.00 mmol) were added, followed by stirring at 100° C. for 15 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, water (20 mL) and ethyl acetate (30 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=0%-20%) to afford the desired compound (835 mg, yield 92%) as a yellow solid.

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=0%-20%)

Sources & evidence

ORD record
ord-bcc72a199add44fa83c7c3169e43e074
Source dataset
uspto-grants-2013_04
Patent number
US08415359B2

Reaction notes

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