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

HRID 2087255

Reaktionsgleichung

Reaktionsgleichung von HRID 2087255
CC(C)(C)C(O[N:6]1[CH2:11][CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH2:8][CH2:7]1)=O.[C:23]([O-:26])([O-])=[O:24].[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:31]=[CH:30][C:35]([CH3:36])=[C:34]([C:9]2[CH2:8][CH2:7][N:6]([C:23]([O:26][C:35]([CH3:36])([CH3:34])[CH3:30])=[O:24])[CH2:11][CH:10]=2)[CH:33]=1)(=[O:42])[CH:39]([CH3:41])[CH3:40]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 22048859N-(3-Bromo-4-methylphenyl)-2-methylpropanamideHCID 220492871-[(2,2-Dimethylpropanoyl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 16756287tert-butyl 4-[5-(isobutyrylamino)-2-methylphenyl]-3,6-dihydro-1(2H)-pyridinecarboxylateAusbeute 124 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a 50-mL RB flask containing 1-[(2,2-dimethylpropanoyl)oxy]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine (500 mg, 1.62 mmol), K2CO3 (670 mg, 4.86 mmol) and PdCl2dppf (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 cooled 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, 62.0%)

Aufarbeitung

  1. temperatureAfter cooled 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-5fff664841814d7e89e1195f96cd606f
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727264B1

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