Triisopropyl borate → HCID 86710788, compound

Temperature

-78 °C

To a stirring solution of 3-bromo-2-(but-3-en-1-yl)pyridine (Ref. Zhang, Z; Dwoskin, L. and Crooks, P. Tetrahedron Lett. 2011, 52, 2667-2669, 550 mg, 2.59 mmol) and triisopropyl borate (0.775 mL, 3.37 mmol) in toluene (4 mL) and THF (1 mL) cooled to −78° C. was added 2.5 M n-BuLi (1.349 mL, 3.37 mmol) over the course of 15 min. During this time period, the reaction color changed from yellow to orange. The reaction was stirred at −78° C. for 2 h then warmed to 0° C. for 15 min. It was then quenched with 2 N HCl (5 mL) and stirred for 10 min. The solution became a slurry (pH was found to be 3). It was then diluted with ether, the ether layer was discared. The aqueous layer was adjusted pH=7-8. A white cloud was formed. It was then extracted with EtOAc, the organic layer was dried over MgSO4, filtered and concentrated to obtain 450 mg (98%) of the desired product as a white foam. LCMS (M+1)=178.1.

1. temperaturethen warmed to 0° C. for 15 min
2. customIt was then quenched with 2 N HCl (5 mL)
3. stirringstirred for 10 min
4. additionIt was then diluted with ether
5. customA white cloud was formed
6. extractionIt was then extracted with EtOAc
7. dry with materialthe organic layer was dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-5ac7756b67b64a4b83c7f5a0ea902362

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08906929B2