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

HRID 2212964Notes

Reaction equation

HRID 2212964 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[S: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>C(N(CC)C=O)C>[F:17][C:13](=[C:12]([F:18])[F:11])[CH2:14][CH2:15][S:10][C:2]1[S:3][C:4]2[C:9]([N:1]=1)=[CH:8][CH:7]=[CH:6][N:5]=2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 178527801HCID 178527801, compound

Product 1

HCID 99216832-(3,4,4-Trifluoro-but-3-enylsulfanyl)-thiazolo[5,4-b]pyridineYield 87.4%

Reagents, catalysts & solvents 1

HCID 12051DiethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of thiazolo[5,4-b]pyridine-2-thiol (6.2 g) in N,N-diethyl formamide under nitrogen was treated with 1,1,2-trifluoro-4-bromobutene (8.3 g) and potassium carbonate (1.5 g), stirred at 60° C. for 24 hours, cooled, and poured into water. The resultant aqueous mixture was extracted with diethyl ether. The organic extract was 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 gave the title product as a colorless oil (8.9 g).

Workup

  1. temperaturecooled
  2. extractionThe resultant aqueous mixture was extracted with diethyl ether
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-a65586e450e1461bb7c0928d705d59c0
Source dataset
uspto-grants-2006_09
Patent number
US07105524B2

Reaction notes

Loading…