Sodium Carbonate → 5-Oxazol-5-yl-pyrazine-2-carboxylic acid
Reaktionsgleichung
C([O-])([O-])=O.[Na+].[Na+].C[O:8][C:9]([C:11]1[CH:16]=[N:15][C:14](Cl)=[CH:13][N:12]=1)=[O:10].CC1(C)C(C)(C)OB([C:26]2[O:30][C:29]([Si](C(C)C)(C(C)C)C(C)C)=[N:28][CH:27]=2)O1>CN(C)C=O>[O:30]1[C:26]([C:14]2[N:15]=[CH:16][C:11]([C:9]([OH:8])=[O:10])=[N:12][CH:13]=2)=[CH:27][N:28]=[CH:29]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
Aqueous Na2CO3 solution (2 M, 14.5 mL) and [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium dichloromethane complex (950 mg) are added to a mixture of 5-chloropyrazine-2-carboxylic acid methyl ester (2.00 g) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-[tris(isopropyl)silyl]-oxazole (4.70 g) in N,N-dimethylformamide (20 mL) under an argon atmosphere. The reaction mixture is stirred over night at 80° C. After cooling to room temperature, the solvents are evaporated, the residue is mixed water and acidified with 4 N hydrochloric acid (12 mL). A precipitate is formed upon addition of ethyl acetate, which is filtered off, washed with ethyl acetate and methanol, and dried. LC (method 7): tR=0.46 min; Mass spectrum (ESI−): m/z=190 [M−H]−.
Aufarbeitung
- temperatureAfter cooling to room temperature
- customthe solvents are evaporated
- additionthe residue is mixed water
- customA precipitate is formed upon addition of ethyl acetate, which
- filtrationis filtered off
- washwashed with ethyl acetate and methanol
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-682feb6dbb594f23b85004f8d104f678
- Quelldatensatz
- uspto-grants-2014_12
- Patentnummer
- US08921398B2
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