Dichloromethane → 4-[5-(1-methyl-1H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1020955Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020955
Br[C:2]1[S:6][C:5]([C:7]2[N:11]=[CH:10][N:9]([CH3:12])[N:8]=2)=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].ClCCl.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])(=O)=O.[Mg+2]>O1CCOCC1>[C:13]([O:17][C:18]([N:20]1[CH2:21][CH:22]=[C:23]([C:2]2[S:6][C:5]([C:7]3[N:11]=[CH:10][N:9]([CH3:12])[N:8]=3)=[CH:4][CH:3]=2)[CH2:24][CH2:25]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]

Komponenten

7

Edukt 5

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 583719633-(5-bromo-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole

Produkt 1

HCID 583719164-[5-(1-methyl-1H-[1,2,4]triazol-3-yl)-thiophen-2-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl esterAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a large pressure flask were charged compound 3-(5-bromo-thiophen-2-yl)-1-methyl-1H-[1,2,4]triazole (3.1 g, 12.8 mmols) (5BW), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (3.6 g, 11.65 mmols), [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium (II), complex with dichloromethane (1:1) (0.475 g, 0.89 mmols), Na2CO3 (8.5 ml) and dioxane (40 ml). The mixture was briefly degassed with Ar for ˜0.5 minute, capped and stirred at 80° C. overnight. After cooling, the reaction mixture was diluted with EtOAc and brine. Organic layer was isolated, and dried MgSO4. After concentration, the residue was purified on silica gel. Elution with EtOAc (100%) gave the desired product (6BW) (3.5 g).

Aufarbeitung

  1. customThe mixture was briefly degassed with Ar for ˜0.5 minute
  2. customcapped
  3. temperatureAfter cooling
  4. additionthe reaction mixture was diluted with EtOAc and brine
  5. customOrganic layer was isolated
  6. concentrationAfter concentration
  7. customthe residue was purified on silica gel
  8. washElution with EtOAc (100%)

Quellen und Nachweise

ORD-Eintrag
ord-d07ee0f111ea4bc68c79d98e4a57c1f4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716483B2

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