4-Fluorophenylhydrazine hydrochloride → HCID 178434457, compound

Participants

Reaction Steps

Prepared by 2-step process from 3-fluoro-4-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-4-yloxy)aniline (prepared as in Example 5, Step D) and 2-methyl-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (prepared according to the 3-step procedure of Example 19, Steps A-C, substituting methylhydrazine for 1-(4-fluorophenyl)hydrazine hydrochloride) according to the procedure of Example 21, Steps A and B. The crude material was purified by silica gel flash column chromatography (3% MeOH in CH2Cl2) to afford 17 mg (64% for 2-step process) of the desired product. LRMS (ESI pos) m/e 395.2 (M+1). 1H-NMR (400 MHz, CD3OD/CDCl3) δ 8.30 (d, 1H), 8.25 (d, 1H), 8.17 (d, 1H), 8.02 (dd, 1H), 7.51 (m, 1H), 7.37 (t, 1H), 6.27 (d, 1H), 3.79 (s, 3H), 2.75 (s, 3H); 19F NMR (376 MHz, CD3OD/CDCl3) δ −128.3.

Provenance & Evidence