Methanol → HCID 86680835, compound

HRID 2401691Notes

Reaction equation

HRID 2401691 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1.[C:21](=O)([O-])[O-:22].[K+].[K+].CO>O>[CH3:21][O:22][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium Carbonate2×HCID 86680834HCID 86680834, compound

Product 1

HCID 86680835HCID 86680835, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.19 g of 3-fluoro-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine, 0.19 g of potassium carbonate and 3 ml of methanol was heated under reflux for 27 hours. To this mixture was added 93 mg of potassium carbonate, and the mixture was further heated under reflux for 2 hours. The reaction mixture was cooled to room temperature. Water was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and washed with saturated brine and dried over magnesium sulfate, then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.16 g of 3-methoxy-4-[5-(trifluoromethyl)benzofuran-2-yl]pyridine (hereinafter, referred to as “Present Active Compound 9”).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 27 hours
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux for 2 hours
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washwashed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ed877dfe5fae4f14a787626dae837575
Source dataset
uspto-grants-2014_08
Patent number
US08796306B2

Reaction notes

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