Sodium bis(trimethylsilyl)amide → 3-Bromo-5-(oxetan-3-YL)pyridine

Temperature

80 °C

To a vial were added (5-bromopyridin-3-yl)boronic acid (110 mg, 0.544 mmol), nickel iodide (5.10 mg, 0.016 mmol), trans-2-aminocyclohexanol hydrochloride (2.473 mg, 0.016 mmol), sodium bis(trimethylsilyl)amide (100 mg, 0.544 mmol) and 2-propanol (0.5 mL). The reaction was stirred under nitrogen for 10 minutes prior to addition of a solution of 3-iodooxetane (50 mg, 0.27 mmol) in 2-propanol (0.2 mL). The vial was sealed and heated at 80° C. overnight. The reaction was then filtered through celite with the aid of ethanol. The solution was concentrated and purified by flash chromatography on silica gel (10-100% ethyl acetate in hexanes) to provide the title compound: LCMS m/z 215.90 [M+2+H]+; 1H NMR (500 MHz, CD3OD) δ 8.56 (s, 1H), 8.51 (s, 1H), 8.19 (s, 1H), 5.11-5.08 (m, 2H), 4.72-4.70 (m, 2H), 4.34-4.29 (m, 1H).

1. customThe vial was sealed
2. filtrationThe reaction was then filtered through celite with the aid of ethanol
3. concentrationThe solution was concentrated
4. custompurified by flash chromatography on silica gel (10-100% ethyl acetate in hexanes)

ORD record

ord-a98b050845b642c2bb492d7a6dcac922

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073929B2