Sodium Carbonate → (+/-)-3-{4-[4-(2-Methyl-piperidin-1-ylmethyl)-oxazol-2-yl]-phenyl}-pyridine

HRID 1445793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445793
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]3[CH3:20])[N:12]=2)=[CH:4][CH:3]=1.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH3:20][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][N:14]1[CH2:13][C:11]1[N:12]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)=[CH:3][CH:4]=2)[O:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 11508283HCID 11508283, Verbindung

Produkt 1

HCID 11537304(+/-)-3-{4-[4-(2-Methyl-piperidin-1-ylmethyl)-oxazol-2-yl]-phenyl}-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1-[2-(4-Bromo-phenyl)-oxazol-4-ylmethyl]-2-methyl-piperidine (See Example 21) (1.0 mmol; N96-A03858-154), 3-pyridyl boronic acid (1.2 mmol), tetrakis-(triphenylphosphine)palladium (0.044 mmol), 2M aqueous sodium carbonate (3 mmol) and dioxane (0.1M) is placed in a microwave reactor vessel with a stirbar. Run the reaction in a CEM microwave reactor at 90° C. with 30 W power and cooling for 30 minutes. After this time, perform an aqueous workup and purify via radial chromatography eluting with 2M ammonia in methanol and dichloromethane to provide the titled compound. MS (m/e): 334.2 (M+1)

Aufarbeitung

  1. customthe reaction in a CEM microwave reactor at 90° C. with 30 W power
  2. temperaturecooling for 30 minutes
  3. custompurify via radial chromatography
  4. washeluting with 2M ammonia in methanol and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-7c9e3552d7144e4e8dbc6595ff67d43a
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666871B2

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