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Trifluoroacetic acid → Methyl 6-(6-methoxy-2-thiophen-3-yl-1H-indol-3-ylmethyl)pyridine-2-carboxylate

HRID 2409944
ノート
印刷プレビュー

反応式

HRID 2409944 の反応式
C(OC([NH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH:17]([C:29](=O)[C:30]1[CH:34]=[CH:33][S:32][CH:31]=1)[CH2:18][C:19]1[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:16][O:15][C:13]1[CH:14]=[C:9]2[C:10]([C:17]([CH2:18][C:19]3[N:24]=[C:23]([C:25]([O:27][CH3:28])=[O:26])[CH:22]=[CH:21][CH:20]=3)=[C:29]([C:30]3[CH:34]=[CH:33][S:32][CH:31]=3)[NH:8]2)=[CH:11][CH:12]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86703269Methyl 6-[2-(2-tert-butoxycarbonylamino-4-methoxyphenyl)-3-oxo-3-thiophen-3-ylpropyl]pyridine-2-carboxylate

生成物 1

HCID 86703270Methyl 6-(6-methoxy-2-thiophen-3-yl-1H-indol-3-ylmethyl)pyridine-2-carboxylate収率 58.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
30 °C

実験手順

To a solution of methyl 6-[2-(2-tert-butoxycarbonylamino-4-methoxyphenyl)-3-oxo-3-thiophen-3-ylpropyl]pyridine-2-carboxylate (2.10 g) in dichloromethane (21 mL) was added dropwise trifluoroacetic acid (4.2 mL) under ice-cooling. This mixture was stirred at 30° C. overnight. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and this solution was washed with a saturated aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (938 mg). 1H-NMR (CDCl3) δ ppm: 3.86 (3H, s), 4.05 (3H, s), 4.54 (2H, s), 6.76 (1H, dd, J=2.2, 8.5 Hz), 6.90 (1H, d, J=2.2 Hz), 7.19-7.24 (1H, m), 7.28-7.35 (2H, m), 7.41 (1H, dd, J=3.0, 5.0 Hz), 7.52 (1H, dd, J=1.3, 3.0 Hz), 7.62 (1H, t, J=7.8 Hz), 7.93-7.98 (1H, m), 8.07 (1H, br s).

後処理

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthis solution was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

出典と根拠

ORDレコード
ord-ffd7c7ad6453480faf7775ff12fddce3
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08815903B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート