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Tetrabutylammonium Fluoride → (Z)-5-(2-fluoro-2-(6-methoxypyridin-3-yl)vinyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1400574
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1400574
[C:1]([N:3]1[C:11]2[CH:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[C:5]2[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][C:4]1=2)#[CH:2].Br[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[N:23][CH:24]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-:44]>O>[F:44]/[C:2](/[C:19]1[CH:24]=[N:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[CH:1]\[N:3]1[C:11]2[CH:10]=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=2[C:5]2[CH2:13][N:14]([CH3:17])[CH2:15][CH2:16][C:4]1=2
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Komponenten

5

Edukt 3

HCID 2724141Tetrabutylammonium FluorideHCID 27348955-Bromo-2-methoxypyridineHCID 594550005-Ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Produkt 1

HCID 59455275(Z)-5-(2-fluoro-2-(6-methoxypyridin-3-yl)vinyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-Ethynyl-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (285 mg, 0.00127 mol) and 5-bromo-2-methoxy-pyridine (200 mg, 0.001063 mol), dichlorobistriphenylphosphine palladium (II) (20 mg, 0.0000285 mol) and TBAF.3H2O (1 g, 0.00317 mol) were charged in a microwave tube. The reaction mixture was heated at 80° C. for 5 min in microwave. It was then cooled to RT. The reaction was monitored by TLC and LCMS. The reaction mixture was diluted with water (100 mL) and the compound extracted with EtOAc (3×30 mL). The combined organic layers were washed with water, dried over sodium sulfate and concentrated under vacuum to obtain the crude product, which was purified on neutral alumina (Eluent: 0-20%, Hexane/EtOAc). 2 mg of pure product was obtained as a liquid. 1H NMR (CDCl3, free base) δ (ppm): 8.22 (s, 1H), 7.92 (d, 1H), 7.36 (d, 1H), 7.20 (s, 1H), 7.04 (d, 1H), 6.80 (d, 1H), 5.70 (d, 1H), 3.68 (s, 2H), 3.92 (m, 2H), 3.88 (m, 2H), 2.60 (s, 3H), 2.42 (s, 3H).

Aufarbeitung

  1. addition3H2O (1 g, 0.00317 mol) were charged in a microwave tube
  2. temperatureIt was then cooled to RT
  3. extractionthe compound extracted with EtOAc (3×30 mL)
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto obtain the crude product, which
  8. customwas purified on neutral alumina (Eluent: 0-20%, Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-8b03ea391f0048b3b5cdfdc7c04ee4d9
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08906925B2

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