4-Bromo-2-ethyl-6-methylaniline → 5-bromo-7-ethyl-1H-indazole

HRID 1880419노트

반응식

HRID 1880419 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([CH2:10][CH3:11])[CH:3]=1.[N:12]([O-])=O.[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([CH2:10][CH3:11])[CH:3]=1)[NH:9][N:12]=[CH:8]2.[Br:1][C:2]1[CH:3]=[C:4]2[C:5](=[C:6]([CH3:8])[CH:7]=1)[NH:9][N:12]=[C:10]2[CH3:11]

참가 물질

5

반응물 2

HCID 9607614-Bromo-2-ethyl-6-methylanilineHCID 23668193Sodium Nitrite

생성물 2

HCID 211021955-bromo-7-ethyl-1H-indazole수율 33%HCID 178434272HCID 178434272, 화합물수율 25%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

A solution of 4-bromo-2-ethyl-6-methylbenzenamine (3.21 g, 15 mmol) in acetic acid (50 mL) was stirred for 3 hours before addition of a 2 M solution of sodium nitrite (11 mL, 22.5 mmol). The resulting mixture was stirred overnight at room temperature. The solution was concentrated and the solid was dissolved in EtOAc and washed with saturated aqueous NaCl (3×). The organic extract was dried over Na2SO4, filtered and concentrated. the crude material was purified by Biotage chromatography (40M, 15-30% EtOAc/heptane) to provide 5-bromo-7-ethyl-1H-indazole (1.11 g, 33%) and 5-bromo-3,7-dimethyl-1H-indazole (0.84 g, 25%).

후처리

  1. concentrationThe solution was concentrated
  2. dissolutionthe solid was dissolved in EtOAc
  3. washwashed with saturated aqueous NaCl (3×)
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe crude material was purified by Biotage chromatography (40M, 15-30% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-80f62e6bf1b04b9891adba1eb644901c
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318762B2

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