Potassium Carbonate → tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 1269139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269139
CC1(C)C(C)(C)OB([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH:14]=2)O1.C([O-])([O-])=O.[K+].[K+].Br[C:30]1[CH:31]=[C:32]([NH:37][C:38](=[O:42])[CH:39]([CH3:41])[CH3:40])[CH:33]=[CH:34][C:35]=1[CH3:36]>CN(C=O)C>[C:38]([NH:37][C:32]1[CH:33]=[CH:34][C:35]([CH3:36])=[C:30]([C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:13][CH:14]=2)[CH:31]=1)(=[O:42])[CH:39]([CH3:41])[CH3:40]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 22048859N-(3-Bromo-4-methylphenyl)-2-methylpropanamide

Produkt 1

HCID 16756287tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylateAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a 50-mL RB-flask containing tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (500 mg, 1.62 mmol), K2CO3 (670 mg, 4.86 mmol) and PdCl2dppf (0.190 mmol, 155 mg) was added a solution of N-(3-bromo-4-methylphenyl)-2-methylpropanamide (415 mg, 1.62 mmol) in DMF (10.0 mL) at room temperature under argon. The mixture was heated to 80° C. under argon overnight. After cooling to room temperature, the mixture was filtered through Celite and the Celite was washed with EtOAc (3×20 mL). The filtrates were washed with H2O (20 mL), brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified flash chromatography (20% EtOAc/hexane) to give tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate (360 mg, 62%): ESMS m/e: 303.0 (M-56+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe mixture was filtered through Celite
  3. washthe Celite was washed with EtOAc (3×20 mL)
  4. washThe filtrates were washed with H2O (20 mL), brine (20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was purified flash chromatography (20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1db37d7c892e484e94ae340e605cb591
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199135B2

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