Diisopropylamine → (2-Methoxypyridin-3-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (1.42 mL, 10 mmol) in THF (10 mL) at 0° C. was added nBuLi (2.5 M, 4.25 mL, 10.6 mmol) dropwise. After stirring at 0° C. for 45 min, a solution of 2-methoxypyridine (0.96 mL, 9.2 mmol) in THF (5 mL) was added, and the mixture was stirred for an additional 1 h before B(OiPr)3 (2.54 mL, 11 mmol) was added. 30 min later, H2O was added to quench the reaction, the THF was removed in vacuo and the aqueous layer was extracted with ether. The aqueous layer was separated, acidified with 48% HBr to pH=4, the resulting precipitates were collected by filtration to yield 2-methoxypyridine-3-ylboronic acid (0.46 g, 40%).

Provenance & Evidence