4-Pyridinecarboxaldehyde → HCID 14743045, compound

To a stirred solution of 2-bromothiophene (10 g, 61.34 mmol) in dry THF (42 mL) was added n-butyl lithium (42.0 mL, 67.48 mmol) dropwise at −78° C. and the mixture was stirred at same temperature for 30 min. Then a solution of isonicotinaldehyde (6.56 g, 61.34 mmol) in dry THF (30 mL) was added dropwise and continued stirring at −78° C. for another 2 h. The reaction mixture was quenched with NH4Cl solution (10 mL), diluted with water (200 mL) and extracted with diethyl ether (2×200 mL). The organic layer was washed with brine (100 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was rotary evaporated under vacuum to get residue which was triturated with mixture of hexane and diethyl ether to get the desired compound as an off-white solid (4 g, 34%); 1H NMR (400 MHz, DMSO-d6) δ 8.52 (dd, J=4.9 Hz, 1.5 Hz, 2H), 7.45-7.38 (m, 3H), 6.97-6.93 (m, 2H), 6.45 (d, J=4.4 Hz, 1H), 5.97 (d, J=4.4 Hz, 1H).

1. stirringcontinued stirring at −78° C. for another 2 h
2. customThe reaction mixture was quenched with NH4Cl solution (10 mL)
3. additiondiluted with water (200 mL)
4. extractionextracted with diethyl ether (2×200 mL)
5. washThe organic layer was washed with brine (100 mL)
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. customThe filtrate was rotary evaporated under vacuum
9. customto get residue which
10. customwas triturated with mixture of hexane and diethyl ether

ORD record

ord-b2729ce89d3d4c9a9ec950d908311648

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062075B2