Extracurricular laboratory: Synthetic route of 101990-70-9

The synthetic route of 101990-70-9 has been constantly updated, and we look forward to future research findings.

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 101990-70-9, name is 5-(Chloromethyl)-2-methoxypyridine, the common compound, a new synthetic route is introduced below. HPLC of Formula: C7H8ClNO

A mixture of N-((1S,2S)-2-hydroxycyclohexyl)-7-methyl-1H-pyrrolo[3,2-b]pyridine-3-carboxamide (Intermediate 13), (120 mg), 5-(chloromethyl)-2-methoxypyridine (69 mg) and cesium carbonate (329 mg) in DMF (3.9 mL) was stirred at rt overnight. A further 20 mg 5-(chloromethyl)-2-methoxypyridine was added and stirred for 2days. A further 100 mg 5-(chloromethyl)-2-methoxypyridine was added and stirred for 24 h. Water (20 mL) was added and the reaction mixture was extracted with EtOAc (3*20 mL). The combined organic layers were washed with brine (20 mL) and dried over MgSO4, filtered and evaporated in vacuo. The residue was purified by column chromatography to give the desired compound (131 mg). LCMS: m/z 395.49 [M+H]+. 1H NMR (400 MHz, CDCl3) ppm 1.15-1.52 ppm (m, 4H) 1.71 (d, J=9.9 Hz, 2H) 2.05 (t, J=9.0 Hz, 2H) 2.50 (s, 3H) 3.16 (br. s., 1H) 3.49 (td, J=9.7, 4.3 Hz, 1H) 3.71-3.84 (m, 1H) 3.83 (s, 3H) 5.43 (s, 2H) 6.62 (d, J=8.6 Hz, 1H) 6.84 (d, J=4.8 Hz, 1H) 7.10 (dd, J=8.6, 2.1 Hz, 1H) 7.79 (d, J=1.8 Hz, 1H) 7.95 (s, 1H) 8.25 (d, J=4.6 Hz, 1H) 9.24 (d, J=7.0 Hz, 1H)

The synthetic route of 101990-70-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Payne, Andrew; Castro Pineiro, Jose Luis; Birch, Louise Michelle; Khan, Afzal; Braunton, Alan James; Kitulagoda, James Edward; Soejima, Motohiro; US2015/94328; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem