Potassium Carbonate → 4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 18189

Reaktionsgleichung

Reaktionsgleichung von HRID 18189
[CH2:1]([C:8]1[C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[C:16](Br)[C:11]=2[O:10][C:9]=1[C:19]#[N:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:21]([O:25][C:26]([N:28]1[CH2:29][CH:30]=[C:31]([C:16]2[C:11]3[O:10][C:9]([C:19]#[N:20])=[C:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[C:12]=3[CH:13]=[C:14]([CH3:18])[CH:15]=2)[CH2:32][CH2:33]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

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 593448943-Benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile

Produkt 1

HCID 593448934-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a flask was added 3-benzyl-7-bromo-5-methyl-benzofuran-2-carbonitrile (0.13 gm, 0.40 mmol), 4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.161 gm, 0.52 mmol), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium (0.020 gm, 0.0245 mmol), and potassium carbonate (0.124 gm, 0.9 mmol). Dimethylfomamide was added via syringe and the mixture evacuated and refilled with nitrogen, then heated for 16 hours at 80° C. The mixture was concentrated under vacuum, water was added, and the mixture was extracted with ethyl acetate. The combined organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give crude 4-(3-benzyl-2-cyano-5-methyl-benzofuran-7-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester as a residue that was used directly in the next step without further characterization.

Aufarbeitung

  1. additionDimethylfomamide was added via syringe
  2. customthe mixture evacuated
  3. additionrefilled with nitrogen
  4. concentrationThe mixture was concentrated under vacuum, water
  5. additionwas added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialThe combined organic phase was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a266461abd1f449d944fb1b31ab42199
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741326B2

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