Water → 2-[(4,4,3-Trifluoro-3-butenyl)thio]thiazolo[4,5-b]pyridine

HRID 1279236Notes

Reaction equation

HRID 1279236 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[SH:10].[F:11][C:12]([F:18])=[C:13]([F:17])[CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[F:11][C:12]([F:18])=[C:13]([F:17])[CH2:14][CH2:15][S:10][C:2]1[S:1][C:9]2[C:4]([N:3]=1)=[N:5][CH:6]=[CH:7][CH:8]=2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 178527821HCID 178527821, compound

Product 1

HCID 98352902-[(4,4,3-Trifluoro-3-butenyl)thio]thiazolo[4,5-b]pyridineYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of thiazolo[4,5-b]pyridine-2-thiol (6.2 g, 0.037 mol) in N,N-dimethylformamide under nitrogen is treated with 1,1,2-trifluoro-4-bromobutene (8.3 g, 0.046 mol) and potassium carbonate (1.5 g), heated to and stirred at 60° C. for 24 hours, cooled, and poured into water. The resultant aqueous mixture is extracted with diethyl ether. The organic extract is dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and a 9:1 hexanes/ethyl acetate solution gives the title product as a colorless oil (8.9 g, 64% yield).

Workup

  1. temperatureheated to and
  2. temperaturecooled
  3. extractionThe resultant aqueous mixture is extracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialis dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

Sources & evidence

ORD record
ord-3a0b758969fd48fbbbe1036f82caa9b3
Source dataset
uspto-grants-2002_09
Patent number
US06448262B1

Reaction notes

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