Lauroyl peroxide → rac-tert-Butyl 8-bromo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

HRID 406261

Reaktionsgleichung

Reaktionsgleichung von HRID 406261
[C:1]1([CH3:31])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[CH2:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:10]3=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.[Br:32]N1C(=O)CCC1=O.C(OOC(=O)CCCCCCCCCCC)(=O)CCCCCCCCCCC>C(Cl)(Cl)Cl>[Br:32][CH:23]1[C:9]2[C:10](=[N:11][C:12]([C:13]3[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=3)=[C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:31])=[CH:6][CH:5]=3)[N:8]=2)[N:20]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[CH2:21][CH2:22]1

Komponenten

5

Edukt 3

HCID 7773Lauroyl peroxideHCID 67184N-bromobutanimideHCID 66666294Tert-butyl 2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Produkt 1

HCID 66666258rac-tert-Butyl 8-bromo-2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl 2,3-dip-tolyl-7,8-dihydropyrido[2,3-b]pyrazine-5(6H)-carboxylate (stepl) (530 mg, 1.275 mmol) in chloroform (10 ml) was added N-bromosuccinimide (272 mg, 1.531 mmol) followed by lauroyl peroxide (50.8 mg, 0.128 mmol) and the mixture was heated to reflux for 1 hour. The solvent was concentrated in vacuo. The crude product was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane to afford the title compound which was used directly into the next step

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. concentrationThe solvent was concentrated in vacuo
  4. customThe crude product was purified by chromatography on silica eluting with 0-50% EtOAc in iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-0e59ea9ff5214e1989337910bed83900
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754085B2

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