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

HRID 1376144ノート

反応式

HRID 1376144 の反応式
[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

参加物

7

反応物 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

生成物 2

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cb33b0f43b1b4511839250fa67ae4ced
出典データセット
uspto-grants-2007_01
特許番号
US07169927B2

反応ノート

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