Potassium Carbonate → 5-(2-Fluoro-4-methoxyphenyl)-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole

Participants

Reaction Steps

A mixture of 5-bromo-6-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazole (600 mg, 1.75 mmol), 2-fluoro-4-methoxyphenylboronic acid (320 mg, 1.88 mmol) and 2 N aqueous potassium carbonate solution (1.8 mL, 3.6 mmol) in 1,4-dioxane (7.2 mL) was purged with N2 three times, treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (66.0 mg, 0.090 mmol) and subjected to microwave irradiation at 90° C. for 40 minutes. The reaction mixture was filtered through Celite, rinsed with EtOAc and concentrated in vacuo. The residue was purified by flash chromatography (0-33% EtOAc/heptane) to provide the title compound (657 mg, 92% yield) as a yellow solid. MS (ES+) 387.3 (M+H)+. 1H NMR (500 MHz, CDCl3) δ 8.09 (s, 1H), 7.62 (s, 1H), 7.52 (s, 1H), 7.19 (t, J=8.54 Hz, 1H), 6.78 (dd, J=8.42, 2.56 Hz, 1H), 6.73 (dd, J=11.47, 2.44 Hz, 1H), 5.75 (s, 2H), 3.87 (s, 3H), 3.64-3.70 (m, 2H), 2.28 (s, 3H), 0.93-1.00 (m, 2H), 0.00 (s, 9H).

Provenance & Evidence