Sodium Carbonate → 2-(4'-Methanesulfinyl-biphenyl-4-yl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole

HRID 1445810

Reaktionsgleichung

Reaktionsgleichung von HRID 1445810
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:12]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:27][S:28]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)=[O:29]>C1(C)C=CC=CC=1.O.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:27][S:28]([C:30]1[CH:35]=[CH:34][C:33]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]([CH3:20])=[C:11]([CH2:13][CH2:14][N:15]4[CH2:19][CH2:18][CH2:17][CH2:16]4)[N:12]=3)=[CH:4][CH:3]=2)=[CH:32][CH:31]=1)=[O:29]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 2773531(4-(Methylsulfinyl)phenyl)boronic acidHCID 116815462-(4-Bromo-phenyl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole

Produkt 1

HCID 116683652-(4'-Methanesulfinyl-biphenyl-4-yl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazoleAusbeute 30,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(4-Bromo-phenyl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole (50 mg, 0.149 mmol), sodium carbonate (47.5 mg, 0.448 mmol) and 4-Methylsulfinylbenzene boronic acid (137.3 mg, 0.75 mmol) in toluene (2.5 mL), water (0.75 mL) and ethanol (1 mL) under nitrogen was added Tetrakis(triphenylphosphine) palladium (0) (17. 2 mg, 0.015 mmol). The reaction was then heated to reflux for 48 h. The reaction was allowed to cool and bound to a SCX-2 cartridge (5 g). The cartridge was washed with one cartridge volume of dimethylformamide and two volumes of methanol. The product was eluted using 2M ammonia in methanol. The ammonia/methanol solution was evaporated on a Genevac® HT4. The sample was further purified by prep-LCMS. The resulting acetonitrile/water fractions were combined and evaporated using a Genevac® HT4 to give 17.8 mg of a colourless oil (30%). MS (m/e): 395.2 (M+1)

Aufarbeitung

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 48 h
  3. temperatureto cool
  4. washThe cartridge was washed with one cartridge volume of dimethylformamide and two volumes of methanol
  5. washThe product was eluted
  6. customThe ammonia/methanol solution was evaporated on a Genevac® HT4
  7. customThe sample was further purified by prep-LCMS
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-62040ce2fea94c37b7258bfd3a19f6ab
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666871B2

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