Benzyl piperazine-1-carboxylate → 4-[5-(4-(benzyloxycarbonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

HRID 41706

Reaktionsgleichung

Reaktionsgleichung von HRID 41706
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21](Br)=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][C:21]([N:38]3[CH2:37][CH2:36][N:35]([C:33]([O:32][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[O:34])[CH2:40][CH2:39]3)=[CH:20][N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 643495Benzyl piperazine-1-carboxylateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 668635404-(5-bromopyridin-2-yl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 668631914-[5-(4-(benzyloxycarbonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl esterAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

10.12 g of 4-(5-bromopyridin-2-yl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester and 5.7 g of 4-(benzyloxycarbonyl)piperazine are placed in 118 ml of toluene and then 0.95 g of tris(dibenzylideneacetone)dipalladium(0), 1.7 g of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and 3.5 g of sodium tert-butoxide are added. The reaction medium is heated at 110° C. for 3 h. Ethyl acetate is subsequently added and the mixture is washed once with water and once with a saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of a mixture of heptane/ethyl acetate (90/10 to 0/100). 10.16 g of 4-[5-(4-(benzyloxycarbonyl)piperazin-1-yl)pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester are obtained.

Aufarbeitung

  1. washthe mixture is washed once with water and once with a saturated aqueous sodium chloride solution
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product obtained
  5. customis chromatographed on silica gel, elution
  6. additionbeing carried out with a gradient of a mixture of heptane/ethyl acetate (90/10 to 0/100)

Quellen und Nachweise

ORD-Eintrag
ord-70fc889aff4a49b78d8ba59c8c67cb0a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530657B2

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