HCID 14743045, compound → HCID 14743046, compound

To a stirred solution of pyridin-4-yl(thiophen-2-yl)methanol (G) (4 g, 20.94 mmol) in acetic acid (40 mL) was added Zn powder (11.69 g, 208.73 mmol) portion wise at 70° C. and the reaction mixture was allowed to reflux for 16 h. Then the reaction mixture was filtered through Celite® and the filtrate was rotary evaporated. The resultant residue was diluted with water (50 mL), basified with Na2CO3 solution to pH 9 at 0° C. and extracted with diethyl ether (2×100 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 the desired compound as an oily liquid (3.2 g, 87%); 1H NMR (400 MHz, DMSO-d6) δ 8.48 (dd, J=1.5 Hz, 4.4 Hz, 2H), 7.37 (dd, J=1.5 Hz, 4.9 Hz, 1H), 7.26 (d, J=5.9 Hz, 2H), 6.99-6.93 (m, 2H), 4.19 (s, 2H).

1. temperatureto reflux for 16 h
2. filtrationThen the reaction mixture was filtered through Celite®
3. additionThe resultant residue was diluted with water (50 mL)
4. custombasified with Na2CO3 solution to pH 9 at 0° C.
5. extractionextracted with diethyl ether (2×100 mL)
6. washThe organic layer was washed with brine (100 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. customThe filtrate was rotary evaporated under vacuum

ORD record

ord-636c058a299c4b12a396012b3b9144f6

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09062075B2