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. 23688-89-3, name is 6-Chloropyrazine-2-carboxylic acid, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Chloropyrazine-2-carboxylic acid
SOCl2 (0.71 mL, 2.84 mmol) and DMF (0.025 mL) were added dropwise to a suspension of 6-chloro-pyrazine -2-carboxylique acid (0.450 g, 2.84 mmol) in toluene (1 mL) and the RM was stirred at 80-90C for 2 h. The solvent was evaporated off under reduced pressure and the residue was dissolved in THF (10 mL) and acetone ( 20 mL), cooled to 0 under argon atmosphere, pyridine ( 0.689 mL, 8.52 mmol), a solution of 4-(trifluoromethoxy)aniline (0.593 mL, 4.42 mmol) in acetone (5 mL) and DMF (1 mL) were added and the RM was stirred at RT overnight. The mixture was treated with aq. 1M HC1 (40 mL) and extracted with EtOAc/TBME (1 :4). The combined extracts were washed with aq. 1M HC1, water, brine and dried over MgSC and the solvent was evaporated off under reduced pressure. The residue was purified by flash chromatography (Silica gel column, 25 g, cyclohexane / EtOAc from 5% to 30% EtOAc) and afforded 6-chloro-N-(4-(trifluoromethoxy)phenyl)pyrazine-2-carboxamide as a yellow oil of which (50 mg, 0.157 mmol), pyrimidin-5-ylboronic acid (39.0 mg, 0.315 mmol), Pd(PPh3)2Cl2 (6.63 mg, 0.0094 mmol), Na2C03 (66.7 mg, 0.630 mmol), DME (668 muGamma), water (191 muGamma) and EtOH (95 mu) was stirred at 80-85C for 1 h. The RM was diluted with THF (2 mL), stirred overnight with Si-Thiol (Silicycle, 124 mg, 0.157 mmol), filtered and the filtrate was evaporated off under reduced pressure to give the crude product which was purified by flash chromatography (Silica gel column, 4 g, DCM / EtOAc + 0.1% NH4OH from 20% to 80% EtOAc+ 0.1% NH4OH) Crystallization from MeOH afforded the title product as white needles. UPLC-MS (Condition 1) tR= 2.68 min, m/z =362.0 [M+H]+, m/z = 360.0 [M-H]”; XH-NMR (400 MHz, DMSO-d6) d ppm 7.45 (d, J=8.6 Hz, 2 H) 8.01 (d, J=9.0 Hz, 2 H) 9.35 (s, 1 H) 9.38 (s, 1 H) 9.69 (s, 1 H) 9.88 (s, 2 H) 10.85 (s, 1 H) .
The synthetic route of 23688-89-3 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NOVARTIS AG; FURET, Pascal; GROTZFELD, Robert Martin; JONES, Darryl Brynley; MANLEY, Paul; MARZINZIK, Andreas; MOUSSAOUI, Saliha; PELLE, Xavier Francois Andre; SALEM, Bahaa; SCHOEPFER, Joseph; WO2013/171641; (2013); A1;,
Pyrazine – Wikipedia,
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