Potassium Carbonate → Tert butyl-5-(2-bromophenyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl(tert-butoxycarbonyl)carbamate

HRID 78613

Reaktionsgleichung

Reaktionsgleichung von HRID 78613
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1B(O)O.Br[C:12]1[N:13]=[C:14]([C:33]2[O:34][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:36][N:37]=2)[C:15]([N:18]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[N:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:21]([O:20][C:19](=[O:25])[N:18]([C:15]1[C:14]([C:33]2[O:34][C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[N:36][N:37]=2)=[N:13][C:12]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])=[CH:17][N:16]=1)[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([CH3:22])([CH3:23])[CH3:24]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2773294(2-Bromophenyl)boronic acidHCID 59471994Tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate

Produkt 1

HCID 59472100Tert butyl-5-(2-bromophenyl)-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl(tert-butoxycarbonyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 15220664Palladium--triphenylphosphane (1/1)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A mixture of (2-bromophenyl)boronic acid (100 mg, 0.4979 mmol), tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (258.1 mg, 0.4979 mmol), potassium carbonate (206.5 mg, 1.494 mmol) and triphenylphosphane palladium (13.06 mg, 11.54 μL, 0.04979 mmol) in DMF (3 mL) was heated at 50° C. for 1 h. The reaction mixture was cooled to room temperature and filtered through a Celite,™ pad. The pad was washed with ethyl acetate (1×10 mL) and the combined filtrates were washed with water (2×10 mL) and brine (1×10 mL), dried over MgSO4 and concentrated to leave the product as a solid which was used directly in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through a Celite,™ pad
  3. washThe pad was washed with ethyl acetate (1×10 mL)
  4. washthe combined filtrates were washed with water (2×10 mL) and brine (1×10 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5aa3b9cc5e2c47e9accd4c77576184eb
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

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