Trifluoroacetic acid → 4-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

HRID 2212771

反応式

HRID 2212771 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH:22]=O)=[CH:16][CH:15]=1.C(O)(C(F)(F)F)=O.C([SiH](CC)CC)C>C(Cl)Cl>[CH3:11][O:12][C:13](=[O:24])[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]=2[CH3:1])=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 72242-MethylindoleHCID 12052TriethylsilaneHCID 10104031Methyl 4-(3-oxopropyl)benzoate

生成物 1

HCID 670554944-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-Methyl-1H-indole (0.86 g, 5.2 mmol) and 4-(3-Oxo-propyl)-benzoic acid methyl ester (1.0 g, 5.2 mmol) in methylene chloride (50 mL), was added TFA (1.78 g, 15.6 mmol), followed by triethylsilane (1.81 g, 15.6 mmol). The reaction mixture was stirred overnight, quenched with sat. NaHCO3 solution (50 mL), and the organic layer was washed with sat. NaHCO3 solution, water, brine, and dried (Na2SO4). Solvent was removed under reduced pressure, and the residue was purified by flash column chromatography with 10–20% EtOAc/hexanes to yield the desired 4-[3-(2-Methyl-1H-indol-3-yl)-propyl]-benzoic acid methyl ester in 88% (1.67 g) yield.

後処理

  1. customquenched with sat. NaHCO3 solution (50 mL)
  2. washthe organic layer was washed with sat. NaHCO3 solution, water, brine
  3. dry with materialdried (Na2SO4)
  4. customSolvent was removed under reduced pressure
  5. customthe residue was purified by flash column chromatography with 10–20% EtOAc/hexanes

出典と根拠

ORDレコード
ord-b54289799a764598b76f6267c4bc6811
出典データセット
uspto-grants-2006_09
特許番号
US07101875B2

関連ノート

読み込み中…