1-Methyl-4-piperidone → 8-chloro-6-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400327ノート

反応式

HRID 1400327 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[C:5]([F:11])[CH:4]=1.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1>S(=O)(=O)(O)O.O1CCOCC1>[Cl:2][C:3]1[CH:4]=[C:5]([F:11])[C:6]2[NH:9][C:16]3[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][C:15]=3[C:7]=2[CH:8]=1

参加物

5

反応物 2

HCID 740491-Methyl-4-piperidoneHCID 2782933(4-Chloro-2-fluorophenyl)hydrazine hydrochloride

生成物 1

HCID 594550388-chloro-6-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid溶媒HCID 312751,4-Dioxane溶媒

実験手順

4-Chloro-2-fluorophenyl hydrazine hydrochloride (1 equiv.) is taken in 7% sulfuric acid in 1,4-dioxan. N-Methylpiperidine-4-one (0.76-1.4 equiv.) is added and the contents are stirred at RT for 10 min. The reaction mixture is then stirred at 100° C. for 6 h. The reaction is monitored by TLC and LCMS. After completion of the reaction, the reaction mixture is concentrated and then slowly quenched with aq. NaHCO3 solution, followed by extraction with EtOAc. The organic layer is dried over anhydrous sodium sulfate and evaporated to dryness. The crude product is purified by column chromatography to afford 8-chloro-6-fluoro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole.

後処理

  1. stirringThe reaction mixture is then stirred at 100° C. for 6 h
  2. customAfter completion of the reaction
  3. concentrationthe reaction mixture is concentrated
  4. customslowly quenched with aq. NaHCO3 solution
  5. extractionfollowed by extraction with EtOAc
  6. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  7. customevaporated to dryness
  8. customThe crude product is purified by column chromatography

出典と根拠

ORDレコード
ord-0d813c50fd7c40f78921045818161a92
出典データセット
uspto-grants-2014_12
特許番号
US08906925B2

反応ノート

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