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

HRID 278022

反応式

HRID 278022 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7416Nitrobenzene溶媒

反応条件

温度
155 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d4fb135a88004116a74448d718e06f2c
出典データセット
uspto-grants-2002_03
特許番号
US06358972B1

関連ノート

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