3-Bromopyridine-4-carboxaldehyde → 1255957-49-3

To a stirred suspension of methyltriphenylphosphonium bromide in dry tetrahydrofuran (15 mL) at 0° C. was added n-butyl lithium (3.87 mL, 3.87 mmol) with constant stirring, yellow colour was observed. The yellow colour suspension was allowed to stir at room temperature for 40 min. After 40 min, the reaction mixture was cooled to 0° C. and 3-bromoisonicotinaldehyde (0.6 g, 3.23 mmol) in tetrahydrofuran (5 mL) was added drop wise, the yellow colour was disappeared. Reaction mass was allowed to stir at 0° C. to room temperature for 3 h. The reaction mixture was diluted with water (30 mL) and extracted with ether (3×25 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate and concentrated under vacuum to afford the crude compound which was purified by column chromatography to obtain the title compound. 1H NMR (400 MHz, CDCl3) δ: 8.69 (s, 1H), 8.45 (d, J=4.8 Hz, 1H), 7.41 (d, J=4.8 Hz, 1H), 7.02-6.95 (m, 1H), 5.95-5.91 (d, J=17.6 Hz, 1H), 5.60-5.57 (d, J=10.8 Hz, 1H). MS (M+2): 185.8.

1. waitAfter 40 min
2. temperaturethe reaction mixture was cooled to 0° C.
3. customReaction mass
4. stirringto stir at 0° C. to room temperature for 3 h
5. extractionextracted with ether (3×25 mL)
6. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
7. dry with materialdried over sodium sulphate
8. concentrationconcentrated under vacuum
9. customto afford the crude compound which
10. customwas purified by column chromatography

ORD record

ord-43284263873149d597868fd001b90374

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073929B2