Reference of 137178-88-2 ,Some common heterocyclic compound, 137178-88-2, molecular formula is C6H3BrClNO, 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.
To a stirred solution/suspension of 5-bromo-2-pyridinecarboxylic acid (0.2 g, 1 mmol) in CH2Cl2 (25 mL) was added oxalyl chloride (0.26 mL, 3 mmol) and 1 drop of DMF. Gas evolved and the all the solids dissolved. After Ih the reaction was evaporated and pumped. This material was dissolved/suspended in CH3CN (10 mL) then Intermediate C (0.25 g, 1 mmol) and diisopropylethylamine (2 mL) were added. A white solid formed(DIEA.HCl). After 1.5 h the reaction was filtered and the filtrate was evaporated, taken up in CH2Cl2, filtered and chromatographed on silica gel, eluting with a gradient of 0-10% methanol +1% ammonium hydroxide in CH2CI2. The product fractions were evaporated, dissolved in CBD2CI2, washed with 1 M NaOH (to remove residual hydrochloride salt) and evaporated to afford 0.25g of 24A (58% yield). 1H NMR (300 MHz, DMSOd5) 69.30 (t, /= 6.4 Hz, IH), 8.78 (d, J= 2.1 Hz, IH), 8.25(dd, J= 2.3 Hz, J= 8.2 Hz, IH), 7.98 (d, J= 8.3 Hz, IH), 7.19 (t, J= 7.8 Hz, IH), 6.88 – 6.80 (m, 2H), 6.74 – 6.68 (m, IH), 4.50 (t, J= 4.9 Hz, IH), 4.43 (d, J= 6.4 Hz, 2H), 3.03 – 2.96 (m, 2H), 2.52 – 2.47 (m, 3H), 2.03 – 1.87 (m, 6H), 1.77 – 1.68 (m, 2H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,137178-88-2, its application will become more common.
Reference:
Patent; ASTRAZENECA AB; WO2007/78251; (2007); A1;,
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