Methanol → 6-(5-(Methylsulfonyl)-1,3,4-thiadiazol-2-yl)isoquinoline

HRID 2075365Notes

Reaction equation

HRID 2075365 reaction equation
CS[C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[N:13][CH:12]=[CH:11]3)=[N:5][N:4]=1.O[O:19][S:20]([O-:22])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+].[CH3:31]O>>[CH3:31][S:20]([C:3]1[S:7][C:6]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[N:13][CH:12]=[CH:11]3)=[N:5][N:4]=1)(=[O:22])=[O:19]

Participants

5

Reactant 4

HCID 887MethanolHCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 579918536-(5-(Methylthio)-1,3,4-thiadiazol-2-yl)isoquinoline

Product 1

HCID 579918986-(5-(Methylsulfonyl)-1,3,4-thiadiazol-2-yl)isoquinolineYield 60%

Procedure

To a 25 mL round bottom flask was added 6-(5-(methylthio)-1,3,4-thiadiazol-2-yl)isoquinoline (0.28 g, 1.1 mmol), Oxone® monopersulfate (2.7 g, 4.3 mmol) and 10 mL of MeOH. The reaction mixture was heated at reflux for 4 hours. Sodium thiosulfate solution (25 mL, 1 M) was added to the mixture. The mixture was then extracted with EtOAc (3×30 mL). The combined organic layers were concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with a gradient of 0 to 90% EtOAc in hexanes) to provide 6-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)isoquinoline (0.19 g, 60%) as a yellow solid. LCMS (M+H) 292 calc. for C12H10N3O2S2 292.0. 1H NMR (400 MHz, CD3OD): δ ppm 2.77-2.79 (m, 3H), 7.19 (d, J=5.67 Hz, 1H), 7.49-7.53 (m, 1H), 7.54-7.58 (m, 1H), 7.78 (d, J=5.87 Hz, 1H), 7.92 (s, 1H), 8.57 (s, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. extractionThe mixture was then extracted with EtOAc (3×30 mL)
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (
  6. washeluting with a gradient of 0 to 90% EtOAc in hexanes)

Sources & evidence

ORD record
ord-01662a99faba423bb3c15aa585274266
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

Loading…