Triacetoxyperiodinane → 1-(4-fluorophenyl)-6-methyl-1H-indazole-5-carbaldehyde

Participants

Reaction Steps

A solution of (1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol (1.14 g, 4.45 mmol) was dissolved in DCM (46 mL) and treated with Dess-Martin periodinane (1.87 g, 4.45 mmol). The reaction was stirred at ambient temperature for about 1 h and filtered over a plug of SiO2 rinsing with DCM (50 mL). The filtrate was partially concentrated under reduced pressure and then filtered over a second plug of SiO2 rinsing with DCM (40 mL). The filtrate was concentrated under reduced pressure and the crude material was purified by column chromatography (EtOAc/heptane 100:0 to 0:60) to afford 1-(4-fluorophenyl)-6-methyl-1H-indazole-5-carbaldehyde (1.09 g, 4.29 mmol, 96%). LC-MS (Table 1, Method g) Rt=2.01 min, m/z 257 (M+H)+. 1H NMR (CDCl3) δ 10.27 (s, 1H), 8.29 (bs, 2H), 7.72-7.63 (m, 2H), 7.45 (s, 1H), 7.32-7.23 (m, 2H), 2.80 (s, 3H).

Provenance & Evidence