Triethylamine → ((E)-2-phenyl-1-trifluoromethylvinyl)amine

HRID 244403

반응식

HRID 244403 반응식
FC1C=CC([N:8]2C3C(=CC(N)=CC=3)C=N2)=CC=1.[F:18][C:19]([F:30])([F:29])[C:20](=O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C.[BH4-].[Na+].[OH-].[Na+]>ClCCl.Cl[Ti](Cl)(Cl)Cl.CO>[C:22]1(/[CH:21]=[C:20](/[NH2:8])\[C:19]([F:30])([F:29])[F:18])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 2229581,1,1-Trifluoro-3-phenyl-2-propanoneHCID 4311764Sodium borohydrideHCID 592357271-(4-Fluorophenyl)-1h-indazol-5-amine

생성물 1

HCID 131731205((E)-2-phenyl-1-trifluoromethylvinyl)amine

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of 100 mg (0.44 mmol) of 1-(4-fluorophenyl)-1H-indazol-5-ylamine in 5 mL of dichloromethane was added 60 μL (1.04 mmol) of 1,1,1-trifluoro-3-phenylpropan-2-one, 70 μL (0.97 mmol) of triethylamine followed by 130 μL (1.02 mmol) of TiCl4. The mixture was stirred for 20 hours and then MeOH was added followed by 200 mg (5.29 mmol) of sodium borohydride. After 1 hour, the mixture was diluted 50 mL of 1N aqueous NaOH and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by Combiflash chromatography using a EtOAc-hexanes (0-70% gradient) to provide 70 mg (37%) of [144-fluorophenyl)-1H-indazol-5-yl]-((E)-2-phenyl-1-trifluoromethylvinyl)amine as a yellow solid.

후처리

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

출처 및 근거

ORD 기록
ord-09aaf42162be40c78eb3df57b20ac493
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658637B2

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