Lithium hydroxide, monohydrate → HCID 59830345, compound

Participants

Reaction Steps

3-Cyanophenylboronic acid (0.4 g, 2.74 mmol), was reacted with Example B38 (0.5 g, 2.74 mmol) in the presence of copper (II) acetate (0.5 g, 2.74 mmol) at 80° C. for 3 hours in pyridine (3.5 ml) to provide ethyl 1-(3-cyanophenyl)-3-isopropyl-1H-pyrazole-5-carboxylate (0.18 g, 24% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.06 (m, 1H), 7.92 (m, 1H), 7.83 (m, 1H), 7.69 (m, 1H), 7.02 (s, 1H), 4.20 (q, J=6 Hz, 1H), 3.00 (m, 1H), 1.26 (d, J=6 Hz, 6H), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 284.2 (M+H+). Hydrolysis of the ester with lithium hydroxide monohydrate provided 1-(3-cyanophenyl)-3-isopropyl-1H-pyrazole-5-carboxylic acid in 94% yield. 1H NMR (400 MHz, DMSO-d6): δ 8.02 (m, 1H), 7.89 (m, 1H), 7.83 (m, 1H), 7.67 (m, 1H), 6.97 (s, 1H), 3.00 (m, 1H), 1.26 (q, J=6 Hz, 6H); MS (ESI) m/z: 256.0 (M+H+).

Provenance & Evidence