Sodium Bicarbonate → HCID 67310689, Verbindung

HRID 1400548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400548
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:29][CH2:28][C:9]2[N:10]([CH2:18][C:19]([C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)(O)[CH3:20])[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1.C(=O)(O)[O-].[Na+]>S(Cl)(Cl)=O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:29][CH2:28][C:9]2[N:10]([CH:18]=[C:19]([C:22]3[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=3)[CH3:20])[C:11]3[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][C:16]=3[C:8]=2[CH2:7]1

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 68486293HCID 68486293, Verbindung

Produkt 1

HCID 67310689HCID 67310689, VerbindungAusbeute 6,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel2×

Versuchsvorschrift

1-[2-(3-Methoxy-propyl)-8-methyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-2-pyridin-4-yl-propan-2-ol (550 mg, 1.39 mmol) was dissolved in thionyl chloride (5 mL), stirred at RT for 1 h. Progress of the reaction was monitored by TLC/LCMS. After completion of the reaction, excess thionyl chloride was evaporated under vacuum. The solid mass obtained was neutralized with aqueous sodium bicarbonate and the desired compound extracted with EtOAc (100 mL×2). The organic layer was dried over anhydrous sodium sulfate, concentrated under vacuum to obtain crude product, which was purified by silica gel column chromatography (100-200 mesh) using MeOH:DCM (0-10%) as eluent followed by reverse phase HPLC to obtain 35 mg of 2-(3-Methoxy-propyl)-8-methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, free base) δ (ppm): 8.62 (d, 2H), 7.42 (d, 2H), 7.22 (s, 1H), 7.10 (s, 1H), 7.0 (s, 2H), 3.80 (s, 2H), 3.50 (t, 2H), 3.36 (s, 3H), 2.92 (m, 2H), 2.78 (m, 4H), 2.42 (s, 3H), 2.02 (s, 3H), 1.95 (m, 2H). 1H NMR (CD3OD oxalate salt) δ (ppm): 8.82 (d, 2H), 8.30 (d, 2H), 7.80 (s, 1H), 7.38 (s, 1H), 7.16 (s, 2H), 4.40 (m, 1H), 3.98 (m, 1H), 3.60 (m, 4H), 3.50 (t, 2H), 3.40 (s, 3H), 3.25 (m, 2H), 2.42 (s, 3H), 2.20 (m, 2H), 2.18 (s, 3H).

Aufarbeitung

  1. customwas evaporated under vacuum
  2. customThe solid mass obtained
  3. extractionthe desired compound extracted with EtOAc (100 mL×2)
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customto obtain crude product, which
  7. customwas purified by silica gel column chromatography (100-200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-7b1ef8e8f2e048d1aecdbc285b1a19b1
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906925B2

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