Sodium hydride → Thiazolo[4,5-b]pyridine,2-[(2,2,2-trifluoroethyl)thio]-

HRID 1279239Notes

Reaction equation

[H-].[Na+].[S:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]1[SH:12].C1(C)C=CC(S(O[CH2:23][C:24]([F:27])([F:26])[F:25])(=O)=O)=CC=1>CN(C)C=O>[F:25][C:24]([F:27])([F:26])[CH2:23][S:12][C:4]1[S:3][C:11]2[C:6]([N:5]=1)=[N:7][CH:8]=[CH:9][CH:10]=2

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of sodium hydride (60% suspension in oil, 0.72 g, 0.03 mol) in N,N-dimethylformamide is cooled to 0° C., treated dropwise with a solution of thiazolo[4,5-b]pyridine-2-thiol (5.0 g, 30 mmol) in N,N-dimethylformamide, stirred for 30 minutes, treated with a solution of 2,2,2-trifluoroethyl p-toluenesulfonate (3.81 g, 15 mmol) in N,N-dimethylformamide, heated to and stirred at 110° C. for 6 hours, and poured into an ice/water mixture. The resultant aqueous mixture is extracted with diethyl ether. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using an ethyl acetate/hexanes solution gives the title product as a light yellow liquid (2.91 g, 39% yield).

Workup

temperatureheated to and
stirringstirred at 110° C. for 6 hours
extractionThe resultant aqueous mixture is extracted with diethyl ether
extractionThe organic extract
washis washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto obtain a residue

Sources & evidence

ORD record: ord-0a40d219543d41dbaf753419cdfcd12a
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448262B1

Reaction notes

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