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

HRID 244403ノート

反応式

HRID 244403 の反応式
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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24193Titanium Tetrachloride触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-09aaf42162be40c78eb3df57b20ac493
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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