2-Nitroaniline → (2-Nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine

HRID 244401ノート

反応式

HRID 244401 の反応式
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[F:11][C:12]([F:32])([F:31])[C:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)[N:19]=[CH:18]2)=O.C(N(CC)CC)C.[BH4-].[Na+]>ClCCl.CO.[OH-].[Na+].Cl[Ti](Cl)(Cl)Cl>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][CH:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([C:24]1[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=1)[N:19]=[CH:18]2)[C:12]([F:31])([F:11])[F:32])([O-:3])=[O:2]

参加物

9

反応物 4

HCID 69462-NitroanilineHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 579432692,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanone

生成物 1

HCID 59437215(2-Nitrophenyl)-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethyl}amine収率 53%

試薬・触媒・溶媒 4

HCID 24193Titanium Tetrachloride触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of 134 mg (0.97 mmol) of 2-nitroaniline in 5 mL of dichloromethane was added 300 mg (0.97 mmol) of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanone, 210 μL (2.9 mmol) of triethylamine, followed by 500 μL 0.5 mmol) of TiCl4. The mixture stirred for 20 hours and was then diluted with methanol followed by 40 mg (1.0 mmol) of sodium borohydride. After 1 hour, the mixture was diluted with 50 mL of 1N aqueous NaOH and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by Combiflash chromatography using EtOAc-hexanes (0-70% gradient) to afford 220 mg (53%) of the title compound as a yellow foam. MS m/z 431 (MH+).

後処理

  1. waitAfter 1 hour
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by Combiflash chromatography

出典と根拠

ORDレコード
ord-d8d1e48177b546049e7f5b004783f78f
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

反応ノート

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