Tert-Butylamine → 8-bromo-N-(tert-butyl)-3-ethylquinoxalin-2-amine

HRID 1056176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056176
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5](Cl)[C:6]([CH2:12][CH3:13])=[N:7]2.[C:15]([NH2:19])([CH3:18])([CH3:17])[CH3:16]>CS(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])[C:6]([CH2:12][CH3:13])=[N:7]2

Komponenten

4

Edukt 2

HCID 6385Tert-ButylamineHCID 897822675-Bromo-3-chloro-2-ethylquinoxaline

Produkt 1

HCID 897847628-bromo-N-(tert-butyl)-3-ethylquinoxalin-2-amineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 5-bromo-3-chloro-2-ethylquinoxaline (312a) (131 mg, 0.48 mmol) and t-butylamine (Aldrich) (0.25 mL, 2.41 mmol) in DMSO (1.0 mL) was stirred under argon in a sealed flask at 100° C. for 17 h. The reaction mixture was then cooled to RT and partitioned between Et2O (80 mL) and saturated aq. NaHCO3 (80 mL). The organic layer was separated and sequentially washed with water (50 mL) and brine (40 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to provide 8-bromo-N-(tert-butyl)-3-ethylquinoxalin-2-amine (136 mg, 0.44 mmol, 92% yield) as a yellow-orange solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.86 (1H, d, J=8.2 Hz), 7.82 (1H, dd, J=7.6, 1.2 Hz), 7.20 (1H, t, J=7.9 Hz), 4.87 (1H, br. s.), 2.84 (2H, q, J=7.4 Hz), 1.64 (9H, s), 1.42 (3H, t, J=7.4 Hz). m/z (ESI, +ve) 308.3/310.3 (M+H)+.

Aufarbeitung

  1. custompartitioned between Et2O (80 mL) and saturated aq. NaHCO3 (80 mL)
  2. customThe organic layer was separated
  3. washsequentially washed with water (50 mL) and brine (40 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fb2d355325464e63a9691b854579f832
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394297B2

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