Application of 885275-59-2 , The common heterocyclic compound, 885275-59-2, name is 6-Chloro-3-iodoimidazo[1,2-a]pyridine, molecular formula is C7H4ClIN2, 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.
A mixture of A-3 (1.00 g, 3.59 mmol), Cul (3.42 g, 17.95 mmol), TMSCF3 (1.53 g, 10.77 mmol) and KF (625.90 mg, 10.77 mmol, 252.38 mu,) in DMF (40.00 mL) was stirred at 95 C for 2 hours under N2, at which point the desired product was observed by LCMS. The mixture was then quenched with 0 (100 mL) and extracted with EtOAc (200 mL x 2). The combined organic layers were washed with 0 (100 mL x 2), brine (100 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by silica gel (PE : EtOAc = 15:1 to EtOAc) to afford A-4 (140.00 mg, 634.69 umol) as a solid. H NMR (CDCI3 400 MHz) delta = 8.28 (s, 1H), 7.98 (d, 1H), 7.69 (d, 1H), 7.37 (dd, lH)..Synthesis of Compound 1: A mixture of A-4 (100.0 mg, 453.35 muiotaetaomicron), [4-(trifluoromethoxy)phenyl]boronic acid (140.04 mg, 680.03 muiotaetaomicron), Pd(i-Bu3P)2 (23.17 mg, 45.34 muiotaetaomicron) and K3P04 (192.47 mg, 906.70 muiotaetaomicron) in dioxane (5.00 mL) and 0 (1.00 mL) was stirred at 80 C for 16 hours under N2. The mixture was then concentrated to give the crude product that was purified by Prep- HPLC to afford Compound 1 (87.14 mg) as a solid. H NMR (400 MHz, CDC13) deltaEta 8.35 (s, 1H), 8.01 (d, 1H), 7.82 (d, 1H), 7.65 – 7.55 (m, 3H), 7.37 (d, 2H). LCMS R, = 1.341 min in 2.0 min chromatography, MS ESI calcd. for [M+H]+ 347.1, found 346.9.
The synthetic route of 885275-59-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; PRAXIS PRECISION MEDICINES, INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew Mark; MARRON, Brian Edward; (168 pag.)WO2018/98500; (2018); A1;,
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