Cesium carbonate → HCID 58958588, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 mL oven dried flask, was added 5-amino-3-tert-butyl-1-methylpyrazole (2.00 g. 13.1 mmol), methyl 2-bromo-5-methoxybenzoate (2.67 g, 10.9 mmol), cesium carbonate (4.96 g, 15.2 mmol), Pd2(dba)3 (337 mg, 0.33 mmol), BINAP (338 mg, 0.54 mmol), and toluene (35 mL). The reaction mixture was degassed, placed under an N2 atmosphere, and then stirred at 110° C. for 16 h. The reaction mixture was cooled to rt, and ethyl acetate (30 mL) was added. The mixture was filtered, the filter cake washed with EtOAc (10 mL), and the filtrate concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (eluent: 10 to 30% EtOAc in hexane) to give the title compound as a light yellow oil (1.34 g, 38%). 1H NMR (400 MHz, CDCl3) δ 1.28 (s, 9H), 3.63 (s, 3H), 3.78 (s, 3H), 3.94 (s, 3H), 5.97 (s, 1H), 6.82 (d, 1H), 7.10 (dd, 1H), 7.47 (d, 1H).

Provenance & Evidence