Iodoethane → HCID 86720181, compound

HRID 1770668Notes

Reaction equation

HRID 1770668 reaction equation
[SH:1][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][CH:6]=[N:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:24](I)[CH3:25]>CN(C=O)C>[CH2:24]([S:1][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][CH:6]=[N:7][CH:8]=2)[N:3]=1)[CH3:25]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178470132HCID 178470132, compound

Product 1

HCID 86720181HCID 86720181, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 2-mercapto-4-methyl-1,6-naphthyridine-3-carboxylate (0.22 g, 0.89 mmol, 1 eq.) in dry DMF (5 ml) was added K2CO3 (0.37 g, 2.66 mmol, 3 eq.) at 0° C. followed by the addition of ethyl iodide (0.41 g, 2.66 mmol, 3 eq.). The reaction mixture was stirred at RT for 1 h. Afterwards the mixture was poured into ice water (10 ml) and extracted with EtOAc (3×20 ml). The combined organic layers were washed with water (20 ml), brine (20 ml), dried over anhydrous Na2SO4 to provide the crude product, which was purified by CC (EtOAc/hexane 2:3) to yield ethyl 2-(ethylthio)-4-methyl-1,6-naphthyridine-3-carboxylate (0.18 g, 0.65 mmol, 73%).

Workup

  1. extractionextracted with EtOAc (3×20 ml)
  2. washThe combined organic layers were washed with water (20 ml), brine (20 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. customto provide the crude product, which
  5. customwas purified by CC (EtOAc/hexane 2:3)

Sources & evidence

ORD record
ord-87bfe7ff046d49c5a35aec15db996be7
Source dataset
uspto-grants-2016_02
Patent number
US09248122B2

Reaction notes

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