Dimethylformamide → 2-[3-(Ethylthio)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

HRID 402337Notes

Reaction equation

HRID 402337 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.[Na].[CH2:22]([SH:24])[CH3:23].CN(C=O)C>O>[CH2:22]([S:24][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)[CH3:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 45051917Sodium ethanethiolHCID 681537072-(3-Fluoropyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine

Product 1

HCID 681540982-[3-(Ethylthio)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridineYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.90 g of 2-(3-fluoropyridin-4-yl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine, 0.32 g of ethylmercaptan sodium salt and 12 ml of DMF was stirred for 1 hour under ice cool. To the reaction mixture was added water, and the deposited solid was collected by filtration. This solid was washed with water, then, dissolved in ethyl acetate. The organic layer was washed with saturated saline, dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 0.89 g of 2-[3-(ethylthio)pyridin-4-yl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter, referred to as the present compound 15).

Workup

  1. temperaturecool
  2. filtrationthe deposited solid was collected by filtration
  3. washThis solid was washed with water
  4. dissolutiondissolved in ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c70149da943e442aacec4a8145fc8b4c
Source dataset
uspto-grants-2014_06
Patent number
US08742112B2

Reaction notes

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