Electric Literature of 4774-14-5, A common heterocyclic compound, 4774-14-5, name is 2,6-Dichloropyrazine, molecular formula is C4H2Cl2N2, 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.
Synthesis of ethyl 4-(3,5-dichloropyrazin-2-yl)benzoate (11b): 2,6-Dichloropyrazine (9) (149 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25 C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) dissolved in THF (2 mL), followed by the addition of ethyl 4-iodobenzoate (359 mg, 1.3 mmol), were then transferred via cannula to the reaction mixture. The reaction mixture was stirred at 25 C. for 1.5 h. with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3¡Á50 mL) and driedanhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:2) furnished compound 11b (251 mg, 87%) as a colourless solid.m.p.: 88.5-90.0 C.1H-NMR (300 MHz, CDCl3) delta: 8.59 (s, 1 H), 8.14 (d, J=8.6 Hz, 2 H), 7.84 (d, J=8.6 Hz, 2 H), 4.40 (q, J=7.2 Hz, 2 H), 1.40 (t, J=7.0 Hz, 3 H).13C-NMR (75 MHz, CDCl3) 6: 165.8, 150.1, 145.9, 142.0, 139.0, 131.6, 129.4 (2), 61.2, 14.3.MS (70 eV, El) m/z (%): 296 (32) [M+], 270 (24), 268 (38), 251 (100), 223 (26).IR (ATR) v (cm-1): 3086, 3005, 2985, 2359, 1966, 1708, 1611, 1569, 1537, 1507, 1482, 1466, 1446, 1423, 1408, 1366, 1310, 1283, 1263, 1190, 1175, 1140, 1131, 1114, 1098, 1028, 1021, 1009, 915, 858, 843, 786, 758, 719, 698, 657, 634, 621, 616, 610, 602.HRMS (El) for C13H10Cl2N2O2 (296.0119): 296.0119.
The synthetic route of 4774-14-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; Knochel, Paul; Mosrin, Marc; US2011/288296; (2011); A1;,
Pyrazine – Wikipedia,
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