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

HRID 1400327노트

반응식

HRID 1400327 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0d813c50fd7c40f78921045818161a92
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906925B2

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