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

HRID 244401노트

반응식

HRID 244401 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 24193Titanium Tetrachloride촉매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-d8d1e48177b546049e7f5b004783f78f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

반응 노트

불러오는 중…