Potassium Phosphate, Tribasic → Tert-Butyl 4-[4-Chloro-2-(2-Methoxy-2-Oxoethyl)Phenyl]-3,6-Dihydropyridine-1(2H)-Carboxylate

HRID 2415540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415540
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.[CH3:23][O:24][C:25](=[O:35])[CH2:26][C:27]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=1Br.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:33][C:31]1[CH:30]=[CH:29][C:28]([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)=[C:27]([CH2:26][C:25]([O:24][CH3:23])=[O:35])[CH:32]=1

Komponenten

6

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 22640779Methyl 2-(2-bromo-5-chlorophenyl)acetate

Produkt 1

HCID 22640774Tert-Butyl 4-[4-Chloro-2-(2-Methoxy-2-Oxoethyl)Phenyl]-3,6-Dihydropyridine-1(2H)-CarboxylateAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A vigorously stirred mixture of the tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (1-4) (1.40 g, 4.53 mmol), methyl(2-bromo-5-chlorophenyl)acetate (1-2) (1.31 g, 4.98 mmol), potassium phosphate tribasic (2.85 g, 13.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.262 g, 0.227 mmol) in N,N-dimethylformamide (22 mL) was degassed via three vacuum/nitrogen ingress cycles and then heated at 100° C. for approximately 18 h. After cooling to room temperature, the reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% ethyl acetate/hexanes as eluent) afforded 1-5 (0.967 g) as a colorless oil.

Aufarbeitung

  1. customwas degassed via three vacuum/nitrogen ingress cycles
  2. temperatureAfter cooling to room temperature
  3. additionthe reaction mixture was poured into water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% ethyl acetate/hexanes as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-5c514bad49a846c9abb888e250e7d281
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06818658B2

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