Triethylamine → 3-Chloropyridine-2-carbonitrile

To a solution of compound 145-B, (22.37 g, 172.7 mmol) in acetonitrile (175 mL) was added triethylamine (48 mL, 346 mmol) and TMS-CN (56 mL, 420 mmol). The solution was heated at reflux for 20 h then evaporated in vacuo. The residue was partitioned between EtOAc (250 mL), 10% aqueous Na2CO3 (50 mL), and filtered over celite. The organic portion of the filtrate was washed with 10% aqueous Na2CO3 (2×50 mL), brine (50 mL), and the organics dried over Na2SO4, filtered, and evaporated in vacuo to afford a dark crystalline residue, which was dissolved in warm diethyl ether (200 mL), filtered, and evaporated in vacuo to afford compound 145-C as a tan-orange powder (23.41 g, 98%). 1H-NMR (DMSO-d6): δ 7.78-7.84 (m, 1H), 8.30 (d, 1H), 8.73 (d, 1H); MS: m/z 139.1 (MH+).

1. temperatureThe solution was heated
2. temperatureat reflux for 20 h
3. customthen evaporated in vacuo
4. customThe residue was partitioned between EtOAc (250 mL), 10% aqueous Na2CO3 (50 mL)
5. filtrationfiltered over celite
6. washThe organic portion of the filtrate was washed with 10% aqueous Na2CO3 (2×50 mL), brine (50 mL)
7. dry with materialthe organics dried over Na2SO4
8. filtrationfiltered
9. customevaporated in vacuo
10. customto afford a dark crystalline residue, which
11. filtrationfiltered
12. customevaporated in vacuo

ORD record

ord-6921b13a67874595a9f67488d1b1657f

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434711B2