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Trifluoroacetic acid → 2-[(4-Chlorophenyl){7-[(methylsulfonyl)methyl]-1H-indol-3-yl}methyl]cyclopropanecarbonitrile

HRID 561695
ノート
印刷プレビュー

反応式

HRID 561695 の反応式
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19](O)[CH:20]2[CH2:22][CH:21]2[C:23]#[N:24])=[CH:15][CH:14]=1.[CH3:26][S:27]([CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:39]=1[NH:38][CH:37]=[CH:36]2)(=[O:29])=[O:28]>ClCCl>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:36]2[C:35]3[C:39](=[C:31]([CH2:30][S:27]([CH3:26])(=[O:29])=[O:28])[CH:32]=[CH:33][CH:34]=3)[NH:38][CH:37]=2)[CH:20]2[CH2:22][CH:21]2[C:23]#[N:24])=[CH:15][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583922947-[(Methylsulfonyl)methyl]-1H-indoleHCID 583923172-[(4-Chlorophenyl)(hydroxy)methyl]cyclopropanecarbonitrile

生成物 1

HCID 583923332-[(4-Chlorophenyl){7-[(methylsulfonyl)methyl]-1H-indol-3-yl}methyl]cyclopropanecarbonitrile

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

95.7 mg (0.43 mmol) of indium(III) chloride and 0.04 ml (0.49 mmol) of trifluoroacetic acid were added to 83.3 mg (0.40 mmol) of the compound from Example 167A and 100 mg (0.25 mmol) of the compound from Example 86A with a purity of 53% under argon in 5 ml of dichloromethane, and the mixture was heated under reflux for three days. It was concentrated and the residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 41.0 mg (33% of theory) of the title compound as mixture of diastereomers.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for three days
  3. concentrationIt was concentrated
  4. customthe residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid)

出典と根拠

ORDレコード
ord-2df2dae686ac4e34bad606665f32948c
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08063234B2

反応ノート

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