Potassium Carbonate → 3-(2-Bromo-3-pyridyl)isoxazole

HRID 1517596Notes

Reaction equation

HRID 1517596 reaction equation
[Br:1][C:2]1[C:7]([C:8]2[CH:12]=[C:11]([Si](C)(C)C)[O:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Br:1][C:2]1[C:7]([C:8]2[CH:12]=[CH:11][O:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86653543[3-(2-Bromo-3-pyridyl)isoxazol-5-yl]-trimethyl-silane

Product 1

HCID 582685393-(2-Bromo-3-pyridyl)isoxazoleYield 29.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [3-(2-bromo-3-pyridyl)isoxazol-5-yl]-trimethyl-silane (620 mg, 2.09 mmol) in methanol (18 mL), potassium carbonate (29.12 mg, 208.59 μmoles) is added in one portion. The mixture is stirred at room temperature for 24 h. The solvent is removed in vacuum. The crude is partitioned between ethyl acetate and saturated solution of ammonium chloride. The organics are washed with water and dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude is purified by normal phase Isco chromatography using as eluent hexane/ethyl acetate from 66/33 to 50/50 as to give 140 mg of title compound as white solid. MS (m/z): 225/227 (M+1/M+3)

Workup

  1. customThe solvent is removed in vacuum
  2. customThe crude is partitioned between ethyl acetate and saturated solution of ammonium chloride
  3. washThe organics are washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude is purified by normal phase Isco chromatography

Sources & evidence

ORD record
ord-3762ecac353d4183aab42dbb9ffbce72
Source dataset
uspto-grants-2012_07
Patent number
US08232289B2

Reaction notes

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