Synthetic Route of 154048-89-2 , The common heterocyclic compound, 154048-89-2, name is N-Boc-3-Amino-4-iodopyridine, molecular formula is C10H13IN2O2, 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.
Alternate Preparation: Tert-butyl 2-((benzyloxy)methyl)-lH-pyrrolo[2,3- c]pyridine-l-carboxylate was also prepared in an alternate preparation directly from tert-butyl tert-butyl (4-iodopyridin-3-yl)carbamate: In a sealed tube was added ((prop-2-yn-l-yloxy)methyl)benzene (104 mu, 0.750 mmol) and tert-butyl (4- iodopyridin-3-yl)carbamate (200 mg, 0.625 mmol) in DMF (625 mu). To this was added PdCl2(PPh3)2 (21.93 mg, 0.031 mmol), copper(I) iodide (11.90 mg, 0.062 mmol) and TEA (1742 mu, 12.50 mmol). This reaction was then degassed for 15 minutes and then allowed to stir at 80 C sealed. After 4 hours the reaction was complete. The reaction mixture was poured into ethyl acetate and saturated ammonium chloride. The organic was collected and washed several times with ammonium chloride. The organic was then purified on the biotage eluting in 10% ethyl acetate for 10 column volumes and then 10%-40% Ethyl acetate in hexanes over 10 column volumes. The product, tert-butyl 2-((benzyloxy)methyl)-lH- pyrrolo[2,3-c]pyridine-l-carboxylate (179 mg, 85% yield) was collected as a dark yellow oil. 1H NMR (400MHz, CHLOROFORM-d) delta = 9.58 – 9.20 (m, 1H), 8.70 – 8.42 (m, 1H), 7.54 – 7.34 (m, 6H), 6.78 (s, 1H), 4.98 (d, J=1.3 Hz, 2H), 4.73 (s, 2H), 1.69 (s, 9H).
The synthetic route of 154048-89-2 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar, M.; OLSON, Richard, E.; MATE, Robert, A.; WO2015/191401; (2015); A1;,
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