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Potassium Carbonate → 4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester

HRID 1747397
ノート
印刷プレビュー

反応式

HRID 1747397 の反応式
[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9]1=[O:17])[CH3:7].[I-].[CH3:20][N:21]1[C:29]2[C:24](=[C:25]([CH3:30])[CH:26]=[CH:27][CH:28]=2)[C:23]([CH2:31][N+](C)(C)C)=[CH:22]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH2:5][CH:6]([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:31][CH:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][C:25]=3[CH3:30])[N:21]([CH3:20])[CH2:22]2)[C:9]1=[O:17])[CH3:7]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 17836486((1,4-Dimethylindole-3-yl)methyl)trimethylammonium iodideHCID 594972784-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid methyl ester

生成物 1

HCID 673593034-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester収率 86.6%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 4-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid methyl ester (85 mg, 0.34 mmol) and (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethylammonium iodide (175 mg, 0.51 mmol) in DMF (2.5 mL) was added K2CO3 (95 mg, 0.69 mmol). The mixture was stirred at 100° C. for 4 hours. The reaction mixture was allowed to cool to room temperature, diluted with EtOAc (50 mL) and washed with H2O (50 mL×3). The organic layer was dried over sodium sulfate and concentrated. The resulting residue was purified by CombiFlash with 25% EtOAc in Hexane as the eluent to afford the desired 4-[3-(1,4-dimethyl-3H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid methyl ester (120 mg, 86%).

後処理

  1. temperatureto cool to room temperature
  2. washwashed with H2O (50 mL×3)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe resulting residue was purified by CombiFlash with 25% EtOAc in Hexane as the eluent

出典と根拠

ORDレコード
ord-00e7819131bb4fe5a7321b2283b4d3c3
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09150556B2

反応ノート

読み込み中…

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