Sodium Carbonate → 3-Fluoro-4-oxazol-5-yl-benzoic acid

HRID 68771

Reaktionsgleichung

Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[F:11].CC1(C)C(C)(C)OB([C:20]2[O:24][C:23]([Si](C(C)C)(C(C)C)C(C)C)=[N:22][CH:21]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O.Cl[Pd]Cl>[F:11][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[C:20]1[O:24][CH:23]=[N:22][CH:21]=1)[C:6]([OH:8])=[O:7]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 4-bromo-3-fluoro-benzoic acid (1.00 g), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2-triisopropylsilanyl-oxazole (1.90 g), PdCl2 [1,1′-bis(diphenylphosphino)-ferrocene]*CH2Cl2 complex (400 mg), and aqueous Na2CO3 solution (2 M; 5.70 mL) in N,N-dimethylformamide (6 mL) is stirred overnight at 80° C. under an argon atmosphere. After cooling to room temperature the reaction mixture is concentrated in vacuo and water is added. The resulting mixture is acidified with hydrochloric acid (4 M; 6 mL) and extracted with ethyl acetate. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is triturated with diethyl ether, filtered off and dried to give the title product. LC (method 1): tR=0.87 min; Mass spectrum (ESI+): m/z=208 [M+H]+.

Aufarbeitung

temperatureAfter cooling to room temperature the reaction mixture
concentrationis concentrated in vacuo and water
additionis added
extractionextracted with ethyl acetate
washThe combined extracts are washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue is triturated with diethyl ether
filtrationfiltered off
customdried

Quellen und Nachweise

ORD-Eintrag: ord-d82ac1979eda48fe8aed6529bddb05a5
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08822471B2

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