Bis(pinacolato)diborane → HCID 86687715, compound

To a round-bottomed flask was added (1,5-cyclooctadiene)(methoxy)-iridium(i) dimer (0.223 g, 0.337 mmol), 4,4-di-tert-butyl-2,2-dipyridyl (0.181 g, 0.674 mmol) and bis(pinacolato)diboron (2.85 g, 11.23 mmol) in heptane (112 ml). The reaction mixture was vacuumed and refilled with dry nitrogen (3×). After stirring for 10 minutes, 2,3-dichloro-6-methoxypyridine (2.0 g, 11.23 mmol) was added. The resulting reaction mixture was stirred at rt overnight. The reaction was diluted with ethyl acetate and washed twice with 1N HCl solution. The organic layer was extracted twice with 1N sodium hydroxide solution, and the combined aqueous layers were acidified with concentrated HCl solution and extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford (5,6-dichloro-2-methoxypyridin-3-yl)boronic acid as an oily light yellow solid. m/z (ESI) 222.1 (M+H)+.

1. additionrefilled with dry nitrogen (3×)
2. customThe resulting reaction mixture
3. stirringwas stirred at rt overnight
4. washwashed twice with 1N HCl solution
5. extractionThe organic layer was extracted twice with 1N sodium hydroxide solution
6. extractionextracted twice with ethyl acetate
7. dry with materialThe combined organic layers were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-dee5be7cbda2434ebf5b15ce6a210b74

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012443B2