4-Fluorobenzene-1,2-diamine → 5-(5-Fluorobenzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole

HRID 278022

반응식

HRID 278022 반응식
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]1)=O.[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([NH2:27])[CH:21]=1>[N+](C1C=CC=CC=1)([O-])=O>[F:19][C:20]1[CH:25]=[CH:24][C:23]2[N:26]=[C:1]([C:3]3[CH:4]=[C:5]4[C:9](=[CH:10][CH:11]=3)[NH:8][CH:7]=[C:6]4[CH:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)[NH:27][C:22]=2[CH:21]=1

참가 물질

4

반응물 2

HCID 1645844-Fluorobenzene-1,2-diamineHCID 226267865-Formyl-3-(1-Methylpiperidin-4-yl)-1H-Indole

생성물 1

HCID 120418115-(5-Fluorobenzimidazol-2-yl)-3-(1-Methylpiperidin-4-yl)-1H-Indole수율 25%

시약·촉매·용매 1

HCID 7416Nitrobenzene용매

반응 조건

온도
155 °C

실험 절차

A solution of 5-formyl-3-(1-methylpiperidin-4-yl)-1H-indole (0.210 g, 0.90 mmol), and 4-fluoro-o-phenylenediamine (0.112 g, 0.90 mmol), in 15 mL of nitrobenzene was heated, with stirring, at 150-160° C. for 24 hours. An additional 0.5 equivalents of the diamine was added, and heating continued for an additional 24 hours. The solution was allowed to cool to room temperature, the solvent was removed in vacuo, and the residue was purified by silica gel chromatography (dichloromethane:methanol 10:1.5) to give the title compound (0.075 g, 25%) as an amorphous tan solid. FDMS m/e=348 (M+). EA calculated for C21H21N4F.¾ H2O: C, 69.69; H, 6.27; N, 15.48. Found: C, 69.61; H, 6.19; N, 15.17.

후처리

  1. temperatureheating
  2. waitcontinued for an additional 24 hours
  3. temperatureto cool to room temperature
  4. customthe solvent was removed in vacuo
  5. customthe residue was purified by silica gel chromatography (dichloromethane:methanol 10:1.5)

출처 및 근거

ORD 기록
ord-d4fb135a88004116a74448d718e06f2c
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358972B1

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