Ethanethiol → HCID 86720178, compound

HRID 1770664Notes

Reaction equation

HRID 1770664 reaction equation
Cl[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH3:17])[C:9]2[C:4](=[CH:5][C:6]([C:18]([F:21])([F:20])[F:19])=[CH:7][N:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28]([SH:30])[CH3:29]>CN(C=O)C.O>[CH2:28]([S:30][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([CH3:17])[C:9]2[C:4](=[CH:5][C:6]([C:18]([F:21])([F:20])[F:19])=[CH:7][N:8]=2)[N:3]=1)[CH3:29]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 86720177HCID 86720177, compound

Product 1

HCID 86720178HCID 86720178, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-chloro-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (0.97 g, 3.05 mmol, 1 eq.) in DMF (10 ml) were added K2CO3 (1.26 g, 9.15 mmol, 3 eq.) and ethanethiol (0.66 ml, 9.15 mmol, 3 eq.) at RT. The mixture was stirred at 60° C. for 16 h. Afterwards the mixture was diluted with water (80 ml) and was extracted with EtOAc (3×80 ml). The combined organic layers were washed with water (100 ml), brine (100 ml), dried over anhydrous Na2SO4 and evaporated to provide the crude product, which is purified by CC (EtOAc/hexane 1:9) to yield ethyl 2-(ethylthio)-4-methyl-7-(trifluoromethyl)-1,5-naphthyridine-3-carboxylate (0.75 g, 2.18 mmol, 71%).

Workup

  1. extractionwas extracted with EtOAc (3×80 ml)
  2. washThe combined organic layers were washed with water (100 ml), brine (100 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated
  5. customto provide the crude product, which
  6. customis purified by CC (EtOAc/hexane 1:9)

Sources & evidence

ORD record
ord-efb864053e954aaab39a24913f2384a8
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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