Pyrazole → 3-Fluoro-2-(1H-pyrazol-1-YL)benzoic acid

HRID 243882

Reaktionsgleichung

[F:1][C:2]1[C:3](I)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[Cs+].[Cs+]>O.[Cu]I.O1CCOCC1>[F:1][C:2]1[C:3]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a mixture of 3-fluoro-2-iodobenzoic acid (1.4 g, 5.26 mmol), 1H-pyrazole (0.72 g, 10.5 mmol), trans-N,N′-dimethyl-cyclohexane-1,2-diamine (0.17 mL, 1.05 mmol), CuI (50.1 mg, 0.26 mmol), dioxane (50 mL) and water (0.028 mL) was added Cs2CO3 (3.43 g, 10.5 mmol). The reaction mixture was heated to 100° C. for 1 h. The reaction mixture was cooled to ambient temperature then diluted with water. The aqueous layer was acidified to pH2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. Purification (FCC), (DCM to 10% MeOH/1% HOAC/DCM) afforded the title compound as a colorless oil (790 mg, 72%). 1H NMR (400 MHz, CDCl3): 7.85-7.73 (m, 1H), 7.54-7.44 (m, 1H), 7.44-7.34 (m, 1H), 6.55 (s, 1H).

Aufarbeitung

temperatureThe reaction mixture was cooled to ambient temperature
extractionextracted with EtOAc (30 mL) three times
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customPurification (FCC), (DCM to 10% MeOH/1% HOAC/DCM)

Quellen und Nachweise

ORD-Eintrag: ord-240730b9b6ba4322a90adcc9efdac7c1
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08653263B2

Verknüpfte Notizen

Wird geladen…