Methanol → 2-(3-Methoxypyridin-4-yl)-5-(trifluoromethyl)benzothiazole

HRID 402331Notes

Reaction equation

HRID 402331 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[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N: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[S:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 671137612-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole

Product 1

HCID 671137652-(3-Methoxypyridin-4-yl)-5-(trifluoromethyl)benzothiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzothiazole, 0.28 g of potassium carbonate and 3 ml of methanol was refluxed with heating for 1.5 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 water and saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 2-(3-methoxypyridin-4-yl)-5-(trifluoromethyl)benzothiazole (hereinafter, referred to as the present compound 4).

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 1.5 hours
  3. extractionthe resultant mixture was extracted with ethyl acetate twice
  4. washThe combined organic layers were washed with water and saturated saline
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a45dab7cfea4057873d6f8838159091
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

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