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

HRID 561575
ノート
印刷プレビュー

反応式

HRID 561575 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:11]2[CH2:13][CH:12]2[C:14]#[N:15])(O)[CH3:9])=[CH:4][CH:3]=1.[CH3:16][S:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:27]=1[NH:26][CH:25]=[CH:24]2.[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:11]2[CH2:13][CH:12]2[C:14]#[N:15])([C:24]2[C:23]3[C:27](=[C:19]([CH2:18][S:17][CH3:16])[CH:20]=[CH:21][CH:22]=3)[NH:26][CH:25]=2)[CH3:9])=[CH:4][CH:3]=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 583921877-[(Methylsulfanyl)methyl]-1H-indoleHCID 583923532-[1-(4-Chlorophenyl)-1-hydroxyethyl]cyclopropanecarbonitrile

生成物 1

HCID 583924532-[1-(4-Chlorophenyl)-1-{7-[(methylsulfanyl)methyl]-1H-indol-3-yl}ethyl]cyclopropanecarbonitrile

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

150 mg (0.68 mmol) of the compound from Example 75A and 120 mg (0.68 mmol) of the compound from Example 8A were introduced into 4 ml of dichloromethane at 0° C., 157 mg (0.71 mmol) of indium(III) chloride were added, and the mixture was stirred at RT for 1 h and under reflux for 0.5 h. After cooling, 0.05 ml (0.68 mmol) of trifluoroacetic acid was added, and the mixture was stirred under reflux for 5 min. It was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride 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 117 mg (45% of theory) of the title compound as mixture of diastereomers.

後処理

  1. temperatureunder reflux for 0.5 h
  2. temperatureAfter cooling
  3. stirringthe mixture was stirred
  4. temperatureunder reflux for 5 min
  5. washwashed with saturated aqueous sodium bicarbonate solution, water and saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. 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-110066f5ea3541aaae724df7c7e12e54
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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