Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 86873-60-1, name is 5-Chloro-2-picolinic acid. A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Chloro-2-picolinic acid
Step 3A. (?)-Methyl 2-(5-chloropicolinamido)-9-methyl-6,7-dihydro-5H- benzo[7]annulene-8-carboxylateTo a solution of 5-chloropicolinic acid (354 mg, 2.248 mmol) in dichloromethane (5 mL) was added HATU (940 mg, 2.473 mmol) and DIPEA (0.589 mL, 3.37 mmol). After stirring for 10 min, methyl 2-amino-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8- carboxylate from preparation J, step Jl (260 mg, 1.124 mmol) was added. The mixture was stirred at rt for 4 h. Ethyl acetate (100 mL) was added and the organic layer was washed with water. After concentration of the organic layer, the residue was purified using silica gel column chromatography (hexanes-100% EtOAc) to give methyl 2-(5- chloropicolinamido)-9-methyl-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate (345 mg, 0.930 mmol, 83 % yield). LCMS (M+H)+ = 371.3. XH NMR (400 MHz, chloroform-if) delta 9.84 (s, IH), 8.56 (dd, J=2.4, 0.6 Hz, IH), 8.25 (dd, J=8.4, 0.6 Hz, IH), 7.88 (dd, J=8.4, 2.4 Hz, IH), 7.73 (d, J=2.3 Hz, IH), 7.63 (dd, J=8.0, 2.3 Hz, IH), 7.20 (d, J=8.3 Hz, IH), 3.82 (s, 3H), 2.55 (t, J=6.5 Hz, 2H), 2.44 (s, 3H), 2.18 – 2.08 (m, 4H).
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Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; THOMPSON III, Lorin A.; SHI, Jianliang; WU, Yong-Jin; MARCIN, Lawrence R.; RAJAMANI, Ramkumar; HIGGINS, Mendi A.; WO2012/162330; (2012); A1;,
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