Sodium hydride → HCID 86663364, compound

To a solution of trimethylsulfoxonium iodide (7.10 g, 32.3 mmol) in DMSO (25 mL) was added NaH (95%, 0.774 g, 32.3 mmol) portionwise at ambient temperature followed by dropwise addition of 5-bromonicotinaldehyde (3.00 g, 16.1 mmol) in DMSO (15 mL) over 15 min. The reaction mixture was quenched by the addition of ice cold water (200 mL) and the resulting mixture extracted with EtOAc (2×150 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by combiflash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes) to obtain 3-bromo-5-(oxiran-2-yl)pyridine (1.00 g, 31.0%) as a pale yellow liquid. LCMS (Condition 8): retention time 1.83 min, [M+2]=202.2. 1H NMR (400 MHz, CDCl3) δ 2.79 (dd, J=2.4 Hz, J=5.2 Hz, 1 H), 3.20 (dd, J=4.0 Hz, J=5.2 Hz, 1 H), 3.87 (dd, J=2.4 Hz, J=4.0 Hz, 1 H), 7.69 (dd, J=1.6 Hz, J=2.0 Hz, 1 H), 8.50 (d, J=1.6 Hz, 1 H), 8.62 (d, J=2.0 Hz, 1 H).

1. customThe reaction mixture was quenched by the addition of ice cold water (200 mL)
2. extractionthe resulting mixture extracted with EtOAc (2×150 mL)
3. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. customThe resulting residue was purified by combiflash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes)

ORD record

ord-fdaa78fc8cf7441196b04fe594506fae

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242966B2