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

HRID 452607노트

반응식

HRID 452607 반응식
[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

참가 물질

6

반응물 3

HCID 1049PyridineHCID 201262(4-Methoxyphenyl)boronic acidHCID 178497374HCID 178497374, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-60e62dab18e345f588baaf8dd48112a6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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