Ethanethiol → HCID 86720183, compound

HRID 1770669Notes

Reaction equation

HRID 1770669 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6](OS(C(F)(F)F)(=O)=O)[N:5]=[C:4]2[S:21][CH:22]=[CH:23][C:3]=12.C([O-])([O-])=O.[K+].[K+].[CH2:30]([SH:32])[CH3:31]>CN(C=O)C.O>[CH2:30]([S:32][C:6]1[N:5]=[C:4]2[S:21][CH:22]=[CH:23][C:3]2=[C:2]([CH3:1])[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:31]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 86720184HCID 86720184, compound

Product 1

HCID 86720183HCID 86720183, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 4-methyl-6-(trifluoro-methyl-sulfonyloxy)thieno[2,3-b]pyridine-5-carboxylate (1.84 g, 4.9 mmol, 1 eq.) in DMF (30 ml) were added K2CO3 (2.70 g, 19.6 mmol, 4 eq.) and ethanethiol (3.73 ml, 49.8 mmol, 10 eq.) at RT. The reaction mixture was stirred at 80° C. for 2 h. Afterwards the mixture was diluted with water (50 ml) and was extracted with EtOAc (2×50 ml). The combined organic layers were washed with water (50 ml), brine (50 ml), dried over Na2SO4 and evaporated. The crude product was purified by CC (EtOAc/hexane 1:49) to yield ethyl 6-(ethylthio)-4-methylthieno[2,3-b]pyridine-5-carboxylate (0.26 g, 0.92 mmol, 19%).

Workup

  1. extractionwas extracted with EtOAc (2×50 ml)
  2. washThe combined organic layers were washed with water (50 ml), brine (50 ml)
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe crude product was purified by CC (EtOAc/hexane 1:49)

Sources & evidence

ORD record
ord-9b4ee1188a3440049bfacdc2b75ef025
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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