Pyridine → HCID 58506460, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,4-dimethoxyphenylboronic acid 1 (2.88 g, 15.8 mmol, 1.00 equiv) in DMF (100 mL) was added methyl 1H-pyrazole-3-carboxylate (3.00 g, 23.7 mmol, 1.50 equiv), Cu(OAc)2 (5.70 g, 31.6 mmol, 2.00 equiv), and pyridine (3.76 g, 47.4 mmol, 3 equiv). The resulting solution was stirred for 2 h at 90° C. The solids were filtrated off by filtration and the filtrate was extracted by EtOAc (200 mL×3). The combined organic layers were dried by anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with PE/EA (3/1). This resulted in 1.5 g (36%) of methyl 1-(2,4-dimethoxyphenyl)-1H-pyrazole-3-carboxylate 2 as a brown solid. 1H NMR (300 MHz, CDCl3): δ 7.88 (d, J=2.4 Hz, 1H), 7.61 (d, J=9 Hz, 1H), 6.97 (d, J=2.4 Hz, 1H), 6.59 (s, 1H), 7.73, 6.58 (d, J=8.7 Hz, 1H). LC-MS: m/z=263 (MH)+.

Provenance & Evidence