Sodium Carbonate → 4-(4-fluorophenyl)-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

Participants

Reaction Conditions

Reaction Steps

4-Bromo-3-methyl-1-(2-methylphenyl)-1H-pyrazol-5-amine (2 g, 7.52 mmol), 4-fluorophenylboronic acid (2.10 g, 11.3 mmol), and Pd(PPh3)4 (434 mg, 0.38 mmol) were dissolved in DMF (20 mL), and Na2CO3 (saturated aq solution, 18 mL) was added. The mixture was degassed for 10 min and then heated at 110° C. for 2 h. The reaction mixture was diluted, and the solid was filtered off. The solvent was concentrated under reduced pressure, and the residue purified by silica gel flash chromatography using 10 to 40% ethyl acetate in hexanes to give 1.2 g (90% pure, 51%) of the title compound. 1H NMR (300 MHz, CD2Cl2) δ 7.25-7.34 (m, 6H), 7.08 (t, 2H), 3.62 (s, 2H), 2.20 (s, 3H), 2.14 (s, 3H).

Provenance & Evidence