Stannous Chloride → 5-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole

HRID 244468

반응식

HRID 244468 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9](=O)[CH3:10])=[C:4]([N+:19]([O-])=O)[CH:3]=1.[Sn](Cl)Cl>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:9]([CH3:10])=[N:19][C:4]=2[CH:3]=1

참가 물질

4

반응물 2

HCID 24479Stannous ChlorideHCID 59437302N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide

생성물 1

HCID 594373055-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole수율 25.2%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
90 °C

실험 절차

To a stirred room temperature solution of N-(4-bromo-2-nitrophenyl)-N-(4-fluorophenyl)acetamide (3.7 g, 10.8 mmol) in ethanol (75 mL) was added tin (II) chloride (6 g, 31.4 mmol) and the mixture was warmed at 90° C. After 3 hours, the mixture was cooled, concentrated in vacuo, diluted with cold water, made basic with 2 N NaOH (pH 11), and extracted with three 75 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a reddish brown oil. The residue was purified by column chromatography over silica gel eluting with 0-50% ethyl acetate in methylene chloride to afford 830 mg of 5-bromo-1-(4-fluorophenyl)-2-methyl-1H-benzimidazole as an off-white solid.

후처리

  1. temperaturethe mixture was cooled
  2. concentrationconcentrated in vacuo
  3. additiondiluted with cold water
  4. extractionextracted with three 75 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a reddish brown oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-50% ethyl acetate in methylene chloride

출처 및 근거

ORD 기록
ord-269ac4b146d64aeabcef2f6db67097bf
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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