Triethylamine → 2-(5-Formyl-isoxazol-3-yl)-pyridine

HRID 2407708Notes

Reaction equation

HRID 2407708 reaction equation
N1C=CC=CC=1.S(=O)(=O)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:21]=[C:20]([CH2:22][OH:23])[O:19][N:18]=1.C(N(CC)CC)C>CS(C)=O.ClCCl.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[CH:21]=[C:20]([CH:22]=[O:23])[O:19][N:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 6865423-(2-Pyridinyl)-5-isoxazolemethanol

Product 1

HCID 226312282-(5-Formyl-isoxazol-3-yl)-pyridineYield 18%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sulfur trioxide pyridine (10.0 g, 62.8 mmol) was dissolved in dimethylsulfoxide (50 mL) and cooled to near 0° C. A solution of the compound prepared in Example 124 (5.05 g, 28.7 mmol) and triethylamine (16.0 mL, 115 mmol) in dichloromethane (40 mL) was added to the solution over 45 minutes. The reaction was warmed to room temperature and stirred overnight. The reaction was diluted with ethyl acetate and washed with sodium hydrogen carbonate aqueous solution. The organic phase was washed with water and dried over magnesium sulfate. The crude mixture was purified by column chromatography using an eluant of 1 to 3% ethyl acetate/dichloromethane to provide the title compound (0.90 g) with the following physical data.

Workup

  1. temperaturecooled
  2. customto near 0° C
  3. washwashed with sodium hydrogen carbonate aqueous solution
  4. washThe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe crude mixture was purified by column chromatography

Sources & evidence

ORD record
ord-13a27517018148cda4c13d12c0b4ee0e
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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