Ethanol → 3-(1-Methyl-1H-pyrazol-4-yl)aniline

3-Bromoaniline (0.50 mL, 4.6 mmol) was dissolved in 30 mL of PhMe with stirring, and 15 mL of EtOH was added. Na2CO3 (3.06 g, 28.9 mmol) in 15 mL of H2O was added followed by 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-1H-pyrazole (0.955 g, 4.59 mmol). Pd(PPh3)4 (0.265 g, 0.229 mmol) was added, and the mixture was heated to reflux with stirring overnight. The mixture was cooled to rt and poured into EtOAc and H2O. The mixture was filtered through celite, and the layers were separated. The organic layer was washed with brine. The organic layer was concentrated and purified by flash chromatography to afford 0.408 g (51%) of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 7.92 (s, 1H), 7.65 (s, 1H), 6.96 (t, J=7.7 Hz, 1H), 6.71-6.64 (m, 2H), 6.41-6.36 (m, 1H), 4.99 (br s, 2H), 3.82 (s, 3H).

1. temperaturethe mixture was heated
2. temperatureto reflux
3. stirringwith stirring overnight
4. filtrationThe mixture was filtered through celite
5. customthe layers were separated
6. washThe organic layer was washed with brine
7. concentrationThe organic layer was concentrated
8. custompurified by flash chromatography

ORD record

ord-3f0014354957416fac62ab3329beaec3

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093239B2