7-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole → 7-[2-(6-methylpyridin-3-yl)ethyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 37787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 37787
[CH3:1][C:2]1[N:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[C:18]3[NH:17][C:16]4[CH:19]5[CH2:25][CH2:24][N:22]([CH2:23][C:15]=4[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:21][CH2:20]5)=[CH:4][CH:3]=1>O=[Pt]=O.C(O)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:18]3[NH:17][C:16]4[CH:19]5[CH2:25][CH2:24][N:22]([CH2:23][C:15]=4[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:21][CH2:20]5)=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 532507617-[(E)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Produkt 1

HCID 532507627-[2-(6-methylpyridin-3-yl)ethyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Adam's catalyst (PtO2, 7 mg, 0.031 mmol; Aldrich) was added to a solution of the product of Example 1D (60 mg, 0.18 mmol) in ethanol (5 mL). The reaction flask was evacuated and purged with nitrogen (3 cycles) then evacuated and purged with hydrogen (4 cycles), and the mixture was stirred under hydrogen (1 atm) at room temperature for 18 hours. The flask was evacuated and purged with nitrogen (3 cycles), and the reaction mixture was filtered. The filtrate was concentrated under vacuum, and the residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 35-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (500 MHz, methanol-d4) δ ppm 2.06 (td, J=7.3, 3.7 Hz, 4 H), 2.45 (s, 3 H), 2.99 (t, J=7.6 Hz, 2 H), 3.01-3.09 (m, 3 H), 3.11 (t, J=7.6 Hz, 2 H), 3.23 (dq, J=7.3, 7.1 Hz, 2 H), 4.20 (s, 2 H), 6.77 (d, J=7.0 Hz, 1 H), 6.88 (t, J=7.5 Hz, 1 H), 7.13 (d, J=7.6 Hz, 1 H), 7.14 (d, J=7.9 Hz, 1 H), 7.49 (dd, J=7.9, 2.1 Hz, 1 H), 8.11 (d, J=1.8 Hz, 1 H); MS (APCI) m/z 332 (M+H)+.

Aufarbeitung

  1. customThe reaction flask was evacuated
  2. custompurged with nitrogen (3 cycles)
  3. customthen evacuated
  4. custompurged with hydrogen (4 cycles)
  5. customThe flask was evacuated
  6. custompurged with nitrogen (3 cycles)
  7. filtrationthe reaction mixture was filtered
  8. concentrationThe filtrate was concentrated under vacuum
  9. customthe residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 35-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)]

Quellen und Nachweise

ORD-Eintrag
ord-faf67b9a1465450a949668a0c2fabe32
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524703B2

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