Potassium Bicarbonate → 3-Bromo-5-(4-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-4,5-dihydroisoxazole

HRID 517915

Reaktionsgleichung

Reaktionsgleichung von HRID 517915
[CH2:1]([N:7]1[C:12]2=[N:13][C:14]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)[N:16]=[C:11]2[CH2:10][CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH:5]=[CH2:6].C(=O)([O-])O.[K+].[Br:36][C:37](Br)=[N:38][OH:39]>CCOC(C)=O>[Br:36][C:37]1[CH2:6][CH:5]([CH2:4][CH2:3][CH2:2][CH2:1][N:7]2[C:12]3=[N:13][C:14]([C:24]4[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=4)=[C:15]([C:17]4[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=4)[N:16]=[C:11]3[CH2:10][CH2:9][CH2:8]2)[O:39][N:38]=1

Komponenten

5

Edukt 3

HCID 516893Potassium BicarbonateHCID 27632191-bromo-N-hydroxymethanecarbonimidoyl bromideHCID 896901775-(Hex-5-enyl)-2,3-dip-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine2×

Produkt 1

HCID 896903823-Bromo-5-(4-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-4,5-dihydroisoxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A mixture comprising 5-(hex-5-enyl)-2,3-di-p-tolyl-5,6,7,8-tetrahydropyrido[2,3-b]pyrazine (Intermediate H) (3.98 g, 10 mmol) and potassium hydrogen carbonate (5.01 g, 50.0 mmol) in EtOAc (50 ml) was treated dropwise with dibromoformaldoxime (6.08 g, 30.0 mmol) in EtOAc (50 ml) over 2 hours. The mixture was stirred at room temperature overnight and then filtered. The filtrate was washed with 1H HCl, water, brine and dried by passing through a phase separator. The solvent was removed under reduced pressure to afford the titled compound which was used without further purification.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtrate was washed with 1H HCl, water, brine
  3. customdried
  4. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e449091dabbd4134ac8d36a5a41f4c7b
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115129B2

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