Potassium Carbonate → 3-Methoxy-6-(indole-2-sulfenyl)-pyridazine

HRID 22727Notes

Reaction equation

HRID 22727 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.Cl[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[NH:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:19][O:18][C:14]1[N:13]=[N:12][C:17]([S:1][C:2]2[NH:3][C:4]3[C:9]([CH:10]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140532121H-indole-2-thiolHCID 225915672-Chloro-6-methoxy-pyridazine

Product 1

HCID 120717643-Methoxy-6-(indole-2-sulfenyl)-pyridazineYield 31%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-mercaptoindole (6.7 mmol, 1.0 g) in acetone (20 mL) was added 2-chloro-6-methoxy-pyridazine (144 mmol, 1.52 g) and potassium carbonate (70 mmol, 0.98 g) and the reaction mixture was refluxed for 2 hours. Excess acetone was removed and the residue was partitioned between CHCl3 (20 mL) and H2O (20 mL). The CHCl3 layer was collected, dried, filtered and the filtrate was evaporated to a residue, which was purified by silica gel chromatography (eluent:hexanes:EtOAc::4:1) to obtain 3-methoxy-6-(indole-2-sulfenyl)-pyridazine (31%, 534 mg).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 hours
  2. customExcess acetone was removed
  3. customthe residue was partitioned between CHCl3 (20 mL) and H2O (20 mL)
  4. customThe CHCl3 layer was collected
  5. customdried
  6. filtrationfiltered
  7. customthe filtrate was evaporated to a residue, which
  8. customwas purified by silica gel chromatography (eluent:hexanes:EtOAc::4:1)

Sources & evidence

ORD record
ord-facc99b90976437685f64213c49e5e26
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Reaction notes

Loading…