Application of 1086838-13-2 , The common heterocyclic compound, 1086838-13-2, name is 5-Chloro-3-nitropicolinaldehyde, molecular formula is C6H3ClN2O3, 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.
a. To a solution of 5-chloro-3-nitropyridine-2-carboxaldehyde (1 g), described in Example 146, in 1,2-dichloroethane (20 mL) was added 4 A molecular sieves powder and 2-(tert-butyldimethylsilanyloxy)propylamine (1.22 g) described in Example 105 part a. After stirring overnight at room temperature, sodium cyanoborohydride (0.4 g) and acetic acid (0.33 mL) were added at 0 C. After stirring for one hour at 0 C., the reaction mixture was heated to 65 C. overnight. The reaction mixture was filtered through a plug of Celite and concentrated under reduced pressure to yield a residue that was purified by chromatography (SiO2, heptane/EA) to afford 2-[2-(tert-butyldimethylsilanyloxy)propyl]-6-chloro-2H-pyrazolo[4,3-b]pyridine (0.6 g, 37%). MS (ES): M/Z [M+H]=326. 1H NMR: (400 MHz, CHLOROFORM-d): -0.37 (s, 3H), -0.09 (s, 3H), 0.79 (s, 9H), 1.24 (d, J=6.1Hz, 3H), 4.21-4.31 (m, 1H), 4.33-4.38 (m, 1H), 4.40-4.47 (m, 1H), 8.00 (dd, J=2.1, 0.9 Hz, 1H), 8.22 (d, J=0.7Hz, 1H) and 8.48 (d, J=2.1Hz, 1H).
The synthetic route of 1086838-13-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; AVENTIS AGRICULTURE; MERIAL LIMITED; Soll, Mark David; Le Hir de Fallois, Loic Patrick; Huber, Scot Kevin; Lee, Hyoung Ik; Wilkinson, Douglas Edward; Jacobs, Robert Toms; US2014/80862; (2014); A1;,
Pyridine – Wikipedia,
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