Triethylamine → HCID 69519303, compound

HRID 1179946Notes

Reaction equation

HRID 1179946 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[N:14][CH:15]=2)=[N:7][CH:8]=1.[I-].C([Si](C)(C)[O:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32](N2C=C[N+](C)=C2)=[O:33])[CH2:28][CH2:27]1)(C)(C)C.C(N(CC)CC)C>C(#N)C>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:32]([N:29]3[CH2:30][CH2:31][CH:26]([OH:25])[CH2:27][CH2:28]3)=[O:33])=[N:14][CH:15]=2)=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 86589184HCID 86589184, compoundHCID 1785162742(1H)-Pyridinone, 5-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-

Product 1

HCID 69519303HCID 69519303, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-(5-trifluoromethyl-pyridin-2-yloxy)-pyridin-2-ol (180 mg, 0.70 mmol), 3-[4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carbonyl]-1-methyl-3H-imidazol-1-ium iodide (317 mg, 0.70 mmol) and triethylamine (98 μL) in acetonitrile (10 mL) was stirred at room temperature overnight. The solvent was evaporated in vacuo. The residue was redissolved in some dichloromethane, filtered over a short pad of silicagel and washed with ethyl acetate:heptane 50:50. The solvent was evaporated in vacuo and the residue was dissolved in 3.2N HCl in ether (10 mL). After stirring for 1 hour at room temperature the solvent was evaporated in vacuo and the residue was dissolved in dichloromethane. Triethylamine (0.5 mL) was added and the solution was extracted with water. The organic layer was dried over sodium sulphate, filtered and evaporated in vacuo to yield the title compound (174 mg, 65% yield) as a thick oil.

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was redissolved in some dichloromethane
  3. filtrationfiltered over a short pad of silicagel
  4. washwashed with ethyl acetate:heptane 50:50
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue was dissolved in 3.2N HCl in ether (10 mL)
  7. customwas evaporated in vacuo
  8. dissolutionthe residue was dissolved in dichloromethane
  9. additionTriethylamine (0.5 mL) was added
  10. extractionthe solution was extracted with water
  11. dry with materialThe organic layer was dried over sodium sulphate
  12. filtrationfiltered
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-a02107e333e94f2ca29f62a229380e0e
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

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