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

HRID 1292965

反応式

HRID 1292965 の反応式
[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

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 215015-Nitroindazole

生成物 1

HCID 219520821-Benzyl-5-nitro-1H-indazole収率 45.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1a4d388626f84811aaef5791b5b36270
出典データセット
uspto-grants-2007_07
特許番号
US07238701B2

関連ノート

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