Reference of 59237-53-5 , The common heterocyclic compound, 59237-53-5, name is Methyl 6-chloro-5-nitronicotinate, molecular formula is C7H5ClN2O4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
[0202] A solution of methyl 6~chloro-5-nitronicotinate (5 g, 23.09 mmol), 4~(2,,4~ difluorophenoxy)piperidine hydrochloride (6.92 g, 27.7 mmol) and K2CO3 (9.57 g, 69.3 mmol) in ACN (57.7 mL) was stirred at 80°C for 5 hours. The reaction mixture was poured into water and extracted with EtOAc (3 x 250 mL). The organic layers were combined, dried over NazSC and filtered. The filtrate was concentrated in vacuo and purified by column chromatography (ISCO column) elutmg with a gradient of 0-100percent EtOAc in heptane, to give the title compound as a yellow solid (6.04 g, 66.5percent). lR NMR (500 MHz, DMSO-afe) delta ppm 1.74 (dq,./ 12. KK. 4.17 Hz, 2 I .}. 2.04 (ddd, J=9.76, 6.83, 3,42 Hz, 2 H), 3.45 (td, 7=8.91, 4.15 Hz, 2 H), 3.71 – 3.76 (m, 2 H), 3.85 (s, 3 H), 4,66 (tt, J=7.51, 3,72 Hz, 1H), 7.00 – 7,06 (m, 1H), 7.27 – 7.36 (m, 2 H), 8.56 (d,/ 1.46 Hz, 1H), 8.82 (d,,/ 1.46 Hz, 1H); ESI-MS m/z | M I I . 394.2.
The synthetic route of 59237-53-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
Pyridine – Wikipedia,
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