Nitrogen → 1-(2,4-Dichlorobenzyl)-6-trifluoromethyl-1H-indazole-3-carboxylic Acid methyl ester

HRID 388625노트

반응식

HRID 388625 반응식
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][CH:12]=2)[NH:7][N:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:26]=1[CH2:27]Cl.N#N>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]([F:17])([F:15])[F:16])=[CH:11][CH:12]=2)[N:7]([CH2:27][C:26]2[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:25]=2[Cl:24])[N:6]=1)=[O:4]

참가 물질

7

반응물 4

HCID 947NitrogenHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium Carbonate2회HCID 53408454Methyl 6-(trifluoromethyl)-1H-indazole-3-carboxylate

생성물 1

HCID 115242041-(2,4-Dichlorobenzyl)-6-trifluoromethyl-1H-indazole-3-carboxylic Acid methyl ester

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6342Acetonitrile용매

실험 절차

6-Trifluoromethyl-1H-indazole-3-carboxylic acid methyl ester (2.75 g, 0.0112 mol) was dissolved in acetonitrile (50 mL), and potassium carbonate (10 g, 0.07 mol), 2,4-dichlorobenzyl chloride (2.42 g, 0.01239 mol) and tetrabutylammonium iodide (catalytic) were added. The reaction mixture was heated to reflux and refluxed for 2 h under good stirring. The progress of the reaction was monitored by TLC. After completion of the reaction, potassium carbonate was filtered while hot and then washed with acetone. The combined solvents were distilled off under reduced pressure to afford the crude mixture of N1 and N2 benzylated products. The isomers were separated by column chromatography (silica gel, eluent started with hexane then changed to 8:2 hexane, ethyl acetate).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperaturerefluxed for 2 h under good stirring
  4. filtrationwas filtered while hot and
  5. washthen washed with acetone
  6. distillationThe combined solvents were distilled off under reduced pressure
  7. customto afford the crude
  8. customThe isomers were separated by column chromatography (silica gel, eluent

출처 및 근거

ORD 기록
ord-7b72b867b9c04661a9bae994f8f73465
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377958B2

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