1222185-12-7 | Pyridine-derivatives

Electric Literature of 1222185-12-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1222185-12-7 as follows.

(E)-Dimethyl 3-styrylpyridine-2,4-dicarboxylate Z4’A stirred suspension of 3-bromopyridine 11 (500 mg, 1.82 mmol, 1 eq.), (E)-styryl boronic acid (300 mg, 2.01 mmol, 1.1 eq.), Cs2CO3 (650 mg, 2.01 mmol, 1.1 eq.), Pd(OAc)2 (40 mg,0.182 mmol, 0.1 eq.) and PPh3 (100 mg, 0.365 mmol, 0.2 eq.) in anhydrous DMF (10 mL) was heated to 70 0C for 5 h in an oil bath. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was dried (Na2SO4) and concentrated in vacuo.The residue was purified by automated flash column chromatography (Biotage KP-SIL SNAP 25 g cartridge, eluting with EpsilontOAc/hexane) to afford Z4′ (322 mg, 60%) as an off-white solid.1U NMR deltaH (400 MHz; CDCl3) 3.86 (s, 3H, OCH3), 3.89 (s, 3Eta, OCH3), 6.59 (d, J=16.5 Hz, IH, CH=CH), 7.23-7.30 (t, J=8.0 Hz, IH, ArHpara), 7.34 (t, J=8.0 Hz, 2H, ArHmeta), 7.46 (d, J=7.0 Hz, 2H, ArHortho), 7.64 (d, J=16.5 Hz, IH, CH=CH), 7.71 (d, J=5.0 Hz, IH, pyHmeta), 8.65 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 52.8 (CH3), 52.8 (CH3), 123.5 (CH=CH), 124.6 (ArCH), 126.7 (ArCH), 128.4 (ArCH), 128.7 (ArCH), 133.0 (ArQ, 135.1 (CH=CH), 136.5 (ArQ, 139.0 (ArQ, 147.9 (ArCH), 149.8 (ArQ, 166.5 (CO), 166.7 (CO); IR vmax (filmycrn 1 2953, 1735, 1447, 1434, 1313, 1269, 1197, 1166, 1143, 1130; HRMS (EpsilonSI+) for C17H15NNaO4 requires 320.0893, found (M+Na*) 320.0893;

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1222185-12-7, its application will become more common.

Reference:
Patent; ISIS INNOVATION LIMITED; SCHOFIELD, Christopher, Joseph; MCDONOUGH, Michael; ROSE, Nathan; THALHAMMER, Armin; WO2010/43866; (2010); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1222185-12-7, name is Dimethyl 3-bromopyridine-2,4-dicarboxylate. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of Dimethyl 3-bromopyridine-2,4-dicarboxylate

Dimethyl 3-phenylpyridine-2,4-dicarboxylate Z3’A stirred suspension of 3-bromopyridine 11 (300 mg, 1.1 mmol, 1 eq.), phenyl boronic acid/anhydride (147 mg, 1.2 mmol, 1.1 eq.), Cs2CO3 (392 mg, 1.2 mmol, 1.1 eq.), Pd(OAc)2 (25 mg, 0.11 mmol, 0.1 eq.) and PPh3 (57 mg, 0.22 mmol, 0.2 eq.) in anhydrous DMF (10 mL) was heated to 70 C for 3 h. The reaction mixture was cooled to room temperature, diluted with water and extracted with EtOAc. The combined organic layers were washed with water, dried(Na2SO4) and concentrated in vacuo. The residue was purified by automated flash column chromatography (Biotage KP-SIL SNAP 25 g cartridge, eluting with EtOAc/hexane) to affordZ3′ (223 mg, 75%) as a light yellow oil.1H NMR deltaH (400 MHz; CDCl3) 3.61 (s, 3H, OCH3), 3.68 (s, 3Eta, OCH3), 7.23 (dd, J=6.5, 3.0 Hz, 2H, ArHmeta), 7.39 (m, 3Eta, ArH), 7.73 (d, J=5.0 Hz, IH, pyHmeta), 8.76 (d, J=5.0 Hz, IH, pyHortho); 13C NMR deltac (100 MHz; CDCl3) 52.6 (CH3), 52.6 (CH3), 124.2 (ArCH), 128.0 (ArCH), 128.2 (ArCH), 128.4 (ArCH), 135.2 (ArQ, 135.7 (ArQ, 140.5 (ArQ, 148.6 (ArCH), 150.8 (ArQ, 166.4 (CO), 166.5 (CO); IR vmax (filmycm 1 3059, 3027, 3003, 2952, 1740, 1434, 1320, 1288, 1199; HRMS (ESI+) for C15H13NNaO4 requires 294.0737, found (M+Na+) 294.0730; 3-PhenyIpyridine-2,4-dicarboxylic acid Z31H NMR deltaH (400 MHz; MeOD) 7.26-7.36 (m, 2H, ArH), 7.38-7.42 (m, 3Eta, ArH), 7.80 (d, J=5.0 Etaz, IH, pyHmeta), 8.69 (d, J=5.0 Etaz, IH, pyHortho); 13C NMR deltac (100 MHz, DMSO-J6) 123.6 (ArCH), 128.8 and 128.9 (2 x ArCH), 129.6 (ArCH), 132.3 (AiQ, 136.4 (ArQ, 142.8 (ArC), 149.2 (ArCH), 153.6 (ArQ, 168.4 (CO), 168.5 (CO); IR Vn^ (KBr diskycm”1 3424, 2920, 2852, 1729, 1612, 1379, 1259, 1192; HRMS (ESI-) for C13H8NO4 requires 242.0459, found (M-H”) 242.0453;

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