Extracurricular laboratory: Synthetic route of 135450-23-6

The synthetic route of 135450-23-6 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. 135450-23-6, name is 6-(Chloromethyl)-2-cyanopyridine, the common compound, a new synthetic route is introduced below. Recommanded Product: 135450-23-6

[00369] 6-((((tert-Butoxy)carbonyl)amino)methyl)picolinonitrile (P31): To a solution of commercially available chloride P30 (9.66 g, 63.3 mmol) in DMF (400 mL) at ambient temperature was treated with potassium phthalimide (11.7 g, 63.3 mmol). After stirring for 5 h, the mixture was concentrated under vacuum. The remaining mixture was taken up in H20 (200 mL) and was filtered to collect the solid. The solid was washed with H20 (100 mL) and THF (100 mL) to obtain the desired phthalimide derivative (11.5 g, 69%) and was moved forward without further purification. To a solution of the crude phthalimide derivative (5.84 g, 22.2 mmol) in THF/MeOH (200 mL, 1:1, v/v) at ambient temperature was treated with hydrazine monohydrate (1.18 mL, 24.4 mmol). After 2 h, 1.0 M HC1 (24.5 mL) was added to the mixture and was stirred for another 3 h before concentrating the reaction mixture under vacuum. The remaining residue was taken up in H20 (200 mL) and the unwanted solid was removed through filtration. The filtrate was concentrated and placed under vacuum to remove the remaining H20. The crude solid was taken up in CH2C12 (175 mL) and triethylamine (9.28 mL, 66.6 mmol) and Boc2O (4.86 g, 24.4 mmol) was added. After stirring for 12 h at room temperature, the reaction was quenched with a saturated solution of NaHCO3 (200 mL), extracted with CH2C12 (3 x 150 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified using flash chromatography (10% to 45% ethyl acetate in hexanes) to provide the aryl pyridine ?IN? fragment (2.24 g, 43%): ?H-NMR (CDC13, 400 MHz) oe 7.78 (t, J = 7.6 Hz, 1H), 7.56 (d, J = 7.6 Hz, 1H), 7.49 (d, J= 8.0 Hz, 1H), 5.51 (s, 1H), 4.44 (d, J= 5.6 Hz, 2H), 1.43 (s, 9H); ?3C-NMR (CDC13, 100 MHz) 160.1, 155.9, 137.6, 133.0, 127.0, 125.1, 117.1, 79.9, 45.5, 28.3; JR (neat) 3347, 2979, 2934, 2239, 1699, 1518, 1453, 1250, 1170, 862; HRMS (ESI) mlz calcd for C12H15N3NaO3 [M+Na1 256.1062, found 256.1062.

The synthetic route of 135450-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; COLORADO STATE UNIVERSITY RESEARCH FOUNDATION; DANA-FARBER CANCER INSTITUTE, INC.; UNIVERSITY OF NOTRE DAME DU LAC; WILLIAMS, Robert, M.; BRADNER, James, E.; CLAUSEN, Dane; WIEST, Olaf, G.; NEWKIRK, Tenaya, L.; BOWERS, Albert, A.; GUERRA, Jennifer, Marie; (144 pag.)WO2016/144665; (2016); A1;,
Pyridine – Wikipedia,
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