Benzyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ylcarbamate → 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

Participants

Reaction Steps

[2-Methoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-3-yl]-carbamic acid benzyl ester (506 mg, 1.32 mmol) was dissolved in methanol (10 mL). Pd(OH)2 on carbon (51 mg, 10 mol %) was added and the reaction was degassed with nitrogen. The nitrogen atmosphere was replaced by hydrogen and the reaction mixture was stirred at room temperature for 5 hours. The palladium residue was removed by filtration through a path of Celite, rinsing with more methanol. The filtrate was concentrated in vacuo to give the title compound as an off-white solid (319 mg, 97% yield). MS (ES+) m/e=251. 1H NMR (DMSO-d6) δH 1.27 (12H, s), 3.88 (3H, s), 4.89 (2H, br s), 7.13 (1H, s), 7.64 (1H, s).

Provenance & Evidence