Ethanol → 2-(3-Ethoxypyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

HRID 402334Notes

Reaction equation

HRID 402334 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][N:11]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:27]([OH:29])[CH3:28]>O>[CH2:27]([O:29][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[S:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:12][N:11]=2)[CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 681537072-(3-Fluoropyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Product 1

HCID 681539672-(3-Ethoxypyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.29 g of 2-(3-fluoropyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine, 0.15 g of potassium carbonate and 6 ml of ethanol was refluxed with heating for 8 hours. The reaction mixture was cooled down to room temperature. To the reaction mixture was added water, and the resultant mixture was extracted with ethyl acetate twice. The combined organic layers were washed with saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 2-(3-ethoxypyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter, referred to as the present compound 11).

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 8 hours
  3. extractionthe resultant mixture was extracted with ethyl acetate twice
  4. washThe combined organic layers were washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0c181b2b7c2c44e2bde5cac00d8ee624
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

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