Imidazole → HCID 84707792、化合物

HRID 1027173

反応式

HRID 1027173 の反応式
N1C=CC=CC=1C1NC2C=CC=CC=2N=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.[Br:27][C:28]1[CH:33]=[CH:32][C:31](I)=[CH:30][C:29]=1[O:35][CH3:36]>[Cu]I.CN(C=O)C>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[CH:30][C:29]=1[O:35][CH3:36]

参加物

7

反応物 4

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 708212-(2'-Pyridyl)benzimidazoleHCID 121872021-Bromo-4-iodo-2-methoxybenzene

生成物 1

HCID 84707792HCID 84707792、化合物収率 67.3%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-(2-pyridyl)benzimidazole (287 mg, 1.469 mmol), cesium carbonate (5.98 g, 18.36 mmol), copper(I) iodide (280 mg, 1.469 mmol) and DMF (5 mL) were combined in a microwave vial fitted with an N2 inlet and magnetic stir bar. The slurry was heated at 60° C. for 1 h, followed by addition of imidazole (500 mg, 7.34 mmol) and 1-bromo-4-iodo-2-methoxybenzene (2.3 g, 7.34 mmol). The reaction mixture was heated at 90° C. for 2 days. The reaction mixture was filtered through celite, washed with EtOAc, and concentrated in vacuo. The crude material was purified by silica gel chromotography (10% to 40% EtOAc in heptanes) to give 1-(4-bromo-3-methoxyphenyl)-1H-imidazole (1.25 g, MS: 255.2 [M+H+])

後処理

  1. customvial fitted with an N2 inlet and magnetic stir bar
  2. temperatureThe reaction mixture was heated at 90° C. for 2 days
  3. filtrationThe reaction mixture was filtered through celite
  4. washwashed with EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by silica gel chromotography (10% to 40% EtOAc in heptanes)

出典と根拠

ORDレコード
ord-108fc876de8445358445d32e5ff57c25
出典データセット
uspto-grants-2014_05
特許番号
US08729263B2

関連ノート

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