Cesium fluoride → 4-(4-Pyrimidin-2-yl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1157169Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1157169
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1)CCC.[F-].[Cs+]>C(PC(C)(C)C)(C)(C)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:26]3[N:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 25953Cesium fluorideHCID 27632512-(Tributylstannyl)pyrimidineHCID 272817821-N-Boc-4-(4-bromophenyl)piperidine

Produkt 1

HCID 595113424-(4-Pyrimidin-2-yl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86614436Di-t-butylphosphine palladiumKatalysator

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture containing 4-(4-bromo-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (100 mg, 0.29 mmol), 2-tributylstannanyl-pyrimidine (130 mg, 0.36 mmol), cesium fluoride (85 mg, 0.56 mmol) and palladium di-tert-butylphosphine was degassed three times with Ar. Dioxane was added and the formed reaction mixture was stirred at 90° C. overnight under Ar. Then the reaction mixture was filter through celite and the solvent was removed under vacuum and crude product was used directly in the next step.

Aufarbeitung

  1. customwas degassed three times with Ar
  2. additionDioxane was added
  3. customthe formed reaction mixture
  4. filtrationThen the reaction mixture was filter through celite
  5. customthe solvent was removed under vacuum and crude product

Quellen und Nachweise

ORD-Eintrag
ord-333b1232f1e24d4cbf5a0e9d3edbb3f1
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807672B2

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