5-Chloro-2-fluoro-4-hydroxybenzaldehyde → 2-Chloro-5-fluoro-4-(6-fluoro-11-methyl-2,3-dihydro-9H-[1,4]dioxino[2,3-f]pyrazolo[3,4-c]isoquinolin-7-yl)phenol

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Reaction Steps

A solution of 4-(7-fluoro-2,3-dihydro-1,4-benzodioxin-5-yl)-3-methyl-1H-pyrazol-5-amine (109 mg, 0.338 mmol) and 5-chloro-2-fluoro-4-hydroxybenzaldehyde (60 mg, 0.338 mmol) in trifluoroacetic acid (2.0 mL) was heated to 75° C. and allowed to stir for 12 h. The reaction mixture was concentrated in vacuo and the residue was purified by reverse phase HPLC to afford 5.8 mg (4.2%) of 2-Chloro-5-fluoro-4-(6-fluoro-11-methyl-2,3-dihydro-9H-[1,4]dioxino[2,3-f]pyrazolo[3,4-c]isoquinolin-7-yl)phenol as a white powder: 1H NMR (400 MHz, d4-MeOH): 7.67 (d, J=7.6 Hz, 1H), 7.07 (d, J=13.2 Hz, 1H), 6.85 (d, J=10.8 Hz, 1H) 4.59-4.56 (m, 4H), 2.99 (s, 3H); MS (EI) for C19H12ClF2N3O3: 404 (MH+).

Provenance & Evidence