Benzyl Bromide → 1-Benzyl-5-nitro-1H-indazole

HRID 1292965

반응식

HRID 1292965 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[CH2:19]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[N:8]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 215015-Nitroindazole

생성물 1

HCID 219520821-Benzyl-5-nitro-1H-indazole수율 45.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

To a solution of 5-nitroindazole (10.0 g, 61.3 mmol) in acetonitrile (100 mL) was added potassium carbonate (16.9 g, 122.6 mmol) and benzyl bromide (13.6 g, 79.7 mmol). The resulting yellow reaction mixture was heated with stirring at 70° C. overnight. Upon cooling down, the solid was filtered off and washed with methylene chloride. The filtrate was concentrated to dryness and the resulting residue was purified by flash chromatography eluting with 17–25% ethyl acetate in hexanes (v/v) yielding 7.0 g (44%) of the corresponding 1-Benzyl-5-nitro-1H-indazole as a yellow solid.

후처리

  1. temperatureThe resulting yellow reaction mixture was heated
  2. temperatureUpon cooling down
  3. filtrationthe solid was filtered off
  4. washwashed with methylene chloride
  5. concentrationThe filtrate was concentrated to dryness
  6. customthe resulting residue was purified by flash chromatography
  7. washeluting with 17–25% ethyl acetate in hexanes (v/v)

출처 및 근거

ORD 기록
ord-1a4d388626f84811aaef5791b5b36270
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238701B2

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