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

HRID 2409944
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HRID 2409944 반응식
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
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참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
30 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ffd7c7ad6453480faf7775ff12fddce3
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08815903B2

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