Sodium hydride → HCID 86663364, compound

To a solution of trimethylsulfoxonium iodide (7.10 g, 32.3 mmol) in DMSO (25 mL) were added, sodium hydride (0.774 g, 32.3 mmol, 95%) (portionwise) at ambient temperature, followed by 5-bromonicotinaldehyde (3.00 g, 16.1 mmol) in DMSO (15 mL). The reaction mixture was quenched by the addition of cold ice water (200 mL) and the resulting mixture extracted with ethyl acetate (2×150 mL). The combined organic layer was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 25% EtOAc/hexanes) to obtain 3-bromo-5-(oxiran-2-yl)pyridine (1.00 g, 31.0%). LCMS Condition B-26: retention time 1.83, [M+2]=202.2. 1H NMR (400 MHz, CDCl3) δ 2.79 (dd, J=2.4 Hz, J=5.2 Hz, 1H), 3.20 (dd, J=4.0 Hz, J=5.2 Hz, 1H), 3.87 (dd, J=2.4 Hz, J=4.0 Hz, 1H), 7.69 (dd, J=1.6 Hz, J=2.0 Hz, 1H), 8.50 (d, J=1.6 Hz, 1H), 8.62 (d, J=2.0 Hz, 1H).

1. customat ambient temperature
2. customThe reaction mixture was quenched by the addition of cold ice water (200 mL)
3. extractionthe resulting mixture extracted with ethyl acetate (2×150 mL)
4. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customto give the residue which
8. customwas purified by column chromatography

ORD record

ord-bbf7680dfa2a463b9dc80927396aee60

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09050345B2