Methanol → 5-chloro-N-{1-[2-(methylsulphinyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide

HRID 1376144Notes

Reaction equation

HRID 1376144 reaction equation
[OH:1][O:2][S:3]([O-:5])=O.[K+].[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([NH:19][CH:20]1[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:30][CH2:31][S:32][CH3:33])[C:21]1=[O:34])=[O:18])=[CH:11]2.[CH3:35]O>O.CCOC(C)=O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([NH:19][CH:20]1[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:30][CH2:31][S:32]([CH3:33])=[O:1])[C:21]1=[O:34])=[O:18])=[CH:11]2.[Cl:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]([NH:19][CH:20]1[CH2:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]([CH2:30][CH2:31][S:3]([CH3:35])(=[O:5])=[O:2])[C:21]1=[O:34])=[O:18])=[CH:11]2

Participants

7

Reactant 3

HCID 887MethanolHCID 101945055-Chloro-N-[1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamideHCID 23707502Potassium hydroxy sulfite

Product 2

HCID 101947795-chloro-N-{1-[2-(methylsulphinyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamideYield 34%HCID 103104305-chloro-N-{1-[2-(methylsulphonyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamideYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Oxone (701 mg, 1.14 mmol) in H2O (12 mL) was added to 5-chloro-N-{1-[2-(methylthio)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (Example 5; 355 mg, 0.86 mmol) in MeOH (12 mL) and stirred for 18 hours. The mixture was diluted with EtOAc (100 mL) washed with saturated NaHCO3 (20 mL), dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (DCM to DCM:THF (3:2) then DCM:MeOH (4:1)) to give 2 yellow solids. Each solid was triturated with refluxing Et2O (25 mL) and the solids filtered, washed with Et2O (25 mL) then hexane (25 mL) to afford 5-chloro-N-{1-[2-(methylsulphinyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (125 mg, 34%) and 5-chloro-N-{1-[2-(methylsulphonyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-1H-indole-2-carboxamide (95 mg, 25%) as white solids.

Workup

  1. washwashed with saturated NaHCO3 (20 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography (DCM to DCM:THF (3:2)
  6. customDCM:MeOH (4:1)) to give 2 yellow solids
  7. customEach solid was triturated with refluxing Et2O (25 mL)
  8. filtrationthe solids filtered
  9. washwashed with Et2O (25 mL)

Sources & evidence

ORD record
ord-cb33b0f43b1b4511839250fa67ae4ced
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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