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

Temperatur

100 °C

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 pH 2 and extracted with EtOAc (30 mL) three times. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAC/DCM) to the yield 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).

1. temperatureThe reaction mixture was cooled to ambient temperature
2. extractionextracted with EtOAc (30 mL) three times
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1% HOAC/DCM) to the

ORD-Eintrag

ord-4a37681f5b8242f9a0c23fb910f94597

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09062044B2