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Potassium Carbonate → 1-{3-[6-Chloro-2-(4-fluorophenyl)-1H-indol-1-yl]-1-oxopropyl}-4-(2-methoxyphenyl)piperazine

HRID 1016656
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HRID 1016656 반응식
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([C:32](=[O:35])[CH:33]=[CH2:34])[CH2:28][CH2:27]1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:8]2[CH2:34][CH2:33][C:32]([N:29]2[CH2:30][CH2:31][N:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[O:19][CH3:18])[CH2:27][CH2:28]2)=[O:35])=[CH:4][CH:3]=1
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 184070336-Chloro-2-(4-fluorophenyl)-1H-indoleHCID 184070531-[4-(2-methoxyphenyl)-1-piperazinyl]-2-Propen-1-one

생성물 1

HCID 102781721-{3-[6-Chloro-2-(4-fluorophenyl)-1H-indol-1-yl]-1-oxopropyl}-4-(2-methoxyphenyl)piperazine

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A mixture of 6-chloro-2-(4-fluorophenyl)-1H-indole (Description 26, 348 mg, 1.4 mmol), 4-(2-methoxyphenyl)-1-(1-oxo-2-propenyl)piperazine (Description 25, 400 mg, 1.6 mmol) and potassium carbonate (1.5 g, 10.8 mmol) in dimethylformamide was stirred at 100° C. for 48 h. The mixture was cooled and aqueous ammonium chloride (saturated, 10 mL) and water (30 mL) were added. The mixture was extracted with ethyl acetate and the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (50:50), to give the title compound. 1H NMR (360 MHz, CDCl3) δ 7.51 (1H, d, J 8.4 Hz), 7.45 (3H, m), 7.18 (2H, t, J 8.7 Hz), 7.11 (1H, dd, J 8.4, 1.8 Hz), 7.01 (1H, m), 6.93-6.81 (3H, m), 6.48 (1H, s), 4.51 (2H, t, J 7.7 Hz), 3.85 (3H, s), 3.72 (2H, t, J 5.0 Hz), 3.30 (2H, t, J 5.0 Hz), 2.93 (2H, t, J 5.0 Hz), 2.79 (2H, t, J 5.0 Hz), and 2.56 (2H, t, J 7.7 Hz). m/z (ES+) 492, 494 (M+1).

후처리

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe combined organic fractions were dried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with isohexane/EtOAc (50:50)

출처 및 근거

ORD 기록
ord-4cfca049d32b4996bcabdeb90434b5dc
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06476045B2

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