Methanol → Methyl 1-(4-fluorophenyl)-6-methyl-1H-indazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 5-bromo-1-(4-fluorophenyl)-6-methyl-1H-indazole (0.29 g, 0.94 mmol), Pd(OAc)2 (0.02 g, 0.09 mmol), dppf (0.10 g, 0.19 mmol) and DMF (5.4 mL). Nitrogen was bubbled through the reaction mixture for about 10 min. The mixture was evacuated and then back-filled with CO three times. Methanol (1.9 mL, 46.9 mmol) and triethylamine (0.65 mL, 4.69 mmol) were added. The reaction mixture was heated, in a sealed microwave vessel, for about 24 h at about 90° C. After cooling to rt, the mixture was partially concentrated under reduced pressure. The residue was partitioned between EtOAc (40 mL) and water (10 mL). The organic layer was washed with brine (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, EtOAc/heptane 100:0 to 0:50) to afford methyl 1-(4-fluorophenyl)-6-methyl-1H-indazole-5-carboxylate (0.25 g, 0.87 mmol, 93%). LC-MS (Table 1, Method g) Rt=2.48 min, m/z 285 (M+H)+. 1H NMR (CDCl3) δ 8.48 (s, 1H), 8.20 (s, 1H), 7.71-7.63 (m, 2H), 7.47 (s, 1H), 7.30-7.20 (m, 2H), 3.93 (s, 3H), 2.74 (s, 3H).

Provenance & Evidence