Trifluoroacetic acid → 2-({7-[(Methylsulfonyl)methyl]-1H-indol-3-yl}[4-(trifluoromethyl)phenyl]methyl)cyclopropane-carbonitrile

HRID 561684ノート

反応式

HRID 561684 の反応式
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.O[CH:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)[CH:14]1[CH2:16][CH:15]1[C:17]#[N:18].[CH3:29][S:30]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:42]=1[NH:41][CH:40]=[CH:39]2)(=[O:32])=[O:31]>ClCCCl.ClCCl>[CH3:29][S:30]([CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[C:38]2[C:42]=1[NH:41][CH:40]=[C:39]2[CH:13]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=1)[CH:14]1[CH2:16][CH:15]1[C:17]#[N:18])(=[O:32])=[O:31]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 159675indium(III)chlorideHCID 583922947-[(Methylsulfonyl)methyl]-1H-indoleHCID 583924082-{Hydroxy[4-(trifluoromethyl)phenyl]methyl}cyclopropanecarbonitrile

生成物 1

HCID 583921232-({7-[(Methylsulfonyl)methyl]-1H-indol-3-yl}[4-(trifluoromethyl)phenyl]methyl)cyclopropane-carbonitrile

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

1.05 g (4.75 mmol) of indium(III) chloride and 0.55 ml (7.12 mmol) of trifluoroacetic acid were added to 954 mg (3.96 mmol) of the compound from Example 160A and 1.02 g (4.75 mmol) of the compound from Example 86A in 60 ml of 1,2-dichloroethane, and the mixture was heated under reflux overnight. It was diluted with dichloromethane and washed with water and saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient with addition of 0.1% formic acid) to result in 197 mg (12% of theory) of the title compound as mixture of diastereomers.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. washwashed with water and saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. 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-b8509878956b48ddaef4cf8b43e0086b
出典データセット
uspto-grants-2011_11
特許番号
US08063234B2

反応ノート

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