Category: 10165-86-3

Application of 10165-86-3 , The common heterocyclic compound, 10165-86-3, name is Methyl 6-formylnicotinate, molecular formula is C8H7NO3, 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.

Example 151C methyl 6-[(1S,3E)-3-[4-(difluoromethoxy)-2-hydroxyphenyl]-1-hydroxy-3-{[(S)-2-methylpropane-2-sulfinyl]imino}propyl]pyridine-3-carboxylate A solution of diisopropylamine (280 muL, 1.965 mmol) in tetrahydrofuran (8 mL) was cooled to 0° C., treated dropwise with 2.5 M n-butyllithium in hexanes (720 muL, 1.801 mmol), stirred at 0° C. for 30 minutes, cooled to -78° C., treated dropwise with a solution of Example 151B (687 mg, 1.637 mmol) in tetrahydrofuran (4 mL), stirred at -78° C. for 45 minutes, treated dropwise with a solution of methyl 6-formylnicotinate (270 mg, 1.637 mmol) in tetrahydrofuran (4 mL), stirred at -78° C. for 1 hour, allowed to warm to -10° C. for 1 hour, treated dropwise with a solution of acetic acid (281 muL, 4.91 mmol) in tetrahydrofuran (1 mL) and partitioned between ethyl acetate (30 mL) and saturated NaHCO3 solution (5 mL). The ethyl acetate layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel, eluting with a gradient of 15percent 100percent ethyl acetate in heptanes to provide products that contained the silyl protecting group (first eluting), followed by the title compound that eluted later. The fractions containing the silyl protecting group were combined, concentrated to dryness, dissolved in tetrahydrofuran (10 mL) under N2, cooled to 0° C., treated with 1 M tetra-n-butylammonium fluoride in tetrahydrofuran (1637 mul, 1.637 mmol) and stirred at 0° C. for 1 hour. The mixture was partitioned between methyl tert-butyl ether (50 mL) and 5percent citric acid solution (25 mL). The methyl tert-butyl ether layer was washed with brine, dried (MgSO4), filtered, and concentrated. The residue was chromatographed on silica gel, eluting with a gradient of 15percent to 100percent ethyl acetate in heptanes to provide more of the title compound. The two portions of title compound were combined to provide 192 mg of title compound. 1H NMR (501 MHz, CDCl3) delta 13.00 (s, 1H), 9.18 (d, J=1.6 Hz, 1H), 8.22 (dd, J=8.2, 2.1 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.54 (d, J=9.1 Hz, 1H), 6.63 (d, J=2.4 Hz, 1H), 6.54 (t, J=73.1 Hz, 1H), 6.47 (dd, J=9.0, 2.5 Hz, 1H), 5.33 (q, J=5.3 Hz, 1H), 4.90 (d, J=5.3 Hz, 1H), 3.96 (s, 3H), 3.80-3.74 (m, 2H), 1.40 (s, 9H); LC/MS (ESI+) m/z 471 (M+H)+.

The synthetic route of 10165-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 10165-86-3, Methyl 6-formylnicotinate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 10165-86-3, blongs to pyridine-derivatives compound. COA of Formula: C8H7NO3

A mixture of methyl 6-formylnicotinate (1.000 g, 6.055 mmol) and 3-chloro-4-fluoroaniline (0.970 g, 6.66 1 mmol) in tetrahydrofuran (50 mL) was stuffed at the room temperature for 30 mm, and treated with sodium triacetoxyborohydride (1.925 g, 9.083 mmol). The reaction mixture was stuffed at the same temperature for additional 18 hr. Then, saturated aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with aqueous saturated sodium chloride solution, dried with anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / dichloromethane = 0 percent to 5 percent) to give methyl6-(((3-chloro-4-fluorophenyl)amino)methyl)nicotinate as brown solid (0.510 g, 28.6percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,10165-86-3, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; HAN, Younghue; KIM, Yuntae; CHOI, Daekyu; MIN, Jaeki; BAE, Miseon; YANG, Hyunmo; KIM, Dohoon; (644 pag.)WO2017/18803; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem