Boronic Acid → (6-(Isobutyramidomethyl)pyridin-3-yl)boronic acid

Participants

Reaction Steps

A mixture N-((5-bromopyridin-2-yl)methyl)isobutyramide (228 mg, 0.887 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (293 mg, 1.153 mmol), PdCl2(dppf)-CH2Cl2Adduct (72.4 mg, 0.089 mmol) and potassium acetate (218 mg, 2.217 mmol) in Dioxane (6 mL) was heated to 70° C. for 3 hr. LCMS indicated that the major product was boronic acid. After cooling to rt, the reaction mixture was filtered through celite and the filtrate was concentrated to afford (6-(isobutyramidomethyl)pyridin-3-yl)boronic acid (195 mg, 0.878 mmol, 99% yield) as a brown oil. The material was used as is in the next step. The yield is assumed to be quantitative. MS (ES+) m/z: 223.1 (M+H); LC retention time: 0.43 min (analytical LCMS Method B).

Provenance & Evidence