5-Chloro-2-fluoro-4-hydroxybenzaldehyde → 2-chloro-5-fluoro-4-(6-fluoro-1-methyl-8,9-dihydro-3H-[1,4]dioxino[2,3-g]pyrazolo[3,4-c]isoquinolin-5-yl)phenol

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Reaction Steps

A solution of 4-(8-fluoro-2,3-dihydro-1,4-benzodioxin-6-yl)-3-methyl-1H-pyrazol-5-amine (100 mg, 0.40 mmol) and 5-chloro-2-fluoro-4-hydroxybenzaldehyde (70 mg, 0.40 mmol) in TFA (2 mL) was stirred at 90° C. for 16 h. The reaction mixture was concentrated and purified by preparative reverse phase HPLC to give 2-chloro-5-fluoro-4-(6-fluoro-1-methyl-8,9-dihydro-3H-[1,4]dioxino[2,3-g]pyrazolo[3,4-c]isoquinolin-5-yl)phenol (18 mg, 11% yield) as a yellow solid after lyophillization of the pure fractions. 1H NMR (400 MHz, d6-DMSO) δ 10.98 (s, 1H), 7.55 (m, 2H), 6.86 (dd, 1H), 4.44 (m, 4H), 2.74 (s, 3H); MS (EI) for C19H12ClF2N3O3: 404 (MH+).

Provenance & Evidence