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Trifluoroacetic acid → 2-[{5-Fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}(4-methylphenyl)methyl]cyclopropane-carbonitrile

HRID 561679
ノート
印刷プレビュー

反応式

HRID 561679 の反応式
[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O.[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([CH2:22][S:23][CH3:24])[CH:21]=1)[NH:18][CH:17]=[CH:16]2.O[CH:26]([C:32]1[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=1)[CH:27]1[CH2:29][CH:28]1[C:30]#[N:31]>ClCCl>[F:12][C:13]1[CH:14]=[C:15]2[C:19](=[C:20]([CH2:22][S:23][CH3:24])[CH:21]=1)[NH:18][CH:17]=[C:16]2[CH:26]([C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=1)[CH:27]1[CH2:29][CH:28]1[C:30]#[N:31]
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 583922275-Fluoro-7-[(methylsulfanyl)methyl]-1H-indoleHCID 583923442-[Hydroxy(4-methylphenyl)methyl]cyclopropanecarbonitrile

生成物 1

HCID 583923752-[{5-Fluoro-7-[(methylsulfanyl)methyl]-1H-indol-3-yl}(4-methylphenyl)methyl]cyclopropane-carbonitrile

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

130 mg (0.59 mmol) of indium(III) chloride and 0.05 ml (0.64 mmol) of trifluoroacetic acid were added to 104 mg (0.53 mmol) of the compound from Example 11A and 100 mg (0.53 mmol) of the compound from Example 158A in 6 ml of dichloromethane, and the mixture was stirred under reflux for 1 h. It was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution and water, 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 39.6 mg (20% of theory) of the title compound as mixture of diastereomers.

後処理

  1. temperatureunder reflux for 1 h
  2. washwashed with saturated aqueous sodium bicarbonate solution and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. 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-fad44e7a140243f39ad8d640476a6c1c
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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