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

HRID 1809328ノート

反応式

HRID 1809328 の反応式
[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]

参加物

7

反応物 4

HCID 947NitrogenHCID 72122,4-Dichlorobenzyl chlorideHCID 11430Potassium Carbonate2 回HCID 53408454Methyl 6-(trifluoromethyl)-1H-indazole-3-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e693f92ff0934aa2a1ad1dcb6fe56920
出典データセット
uspto-grants-2013_01
特許番号
US08362031B2

反応ノート

読み込み中…