Pyridine → methyl 1-(4-methoxyphenyl)-1H-benzimidazole-6-carboxylate

HRID 452607ノート

反応式

HRID 452607 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:3]2[C:4]3[CH:9]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[CH:7]=[CH:6][C:5]=3[N:1]=[CH:2]2)=[CH:18][CH:17]=1

参加物

6

反応物 3

HCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 178497374HCID 178497374、化合物

生成物 1

HCID 68664448methyl 1-(4-methoxyphenyl)-1H-benzimidazole-6-carboxylate収率 13%

試薬・触媒・溶媒 2

HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

A suspension of methyl 1H-benzimidazole-5-carboxylate (10.4 g, 58.8 mmol), (4-methoxyphenyl)boronic acid (17.9 g, 118 mmol), copper(II) acetate (16.0 g, 88.2 mmol), pyridine (9.54 mL, 118 mmol) and molecular sieves 4A (24.0 g) in dichloromethane (240 mL) was stirred at room temperature for 6 hr. The reaction mixture was filtered, and the filtrate was washed with 5% aqueous ammonia and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/ethyl acetate=5/1) and recrystallized from hexane/ethyl acetate to give the title compound (2.15 g, yield 13%) as colorless crystals.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe filtrate was washed with 5% aqueous ammonia and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (dichloromethane/ethyl acetate=5/1)
  6. customrecrystallized from hexane/ethyl acetate

出典と根拠

ORDレコード
ord-60e62dab18e345f588baaf8dd48112a6
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

読み込み中…