A new synthetic route of 3-Amino-4-iodopyridine

According to the analysis of related databases, 105752-11-2, the application of this compound in the production field has become more and more popular.

Reference of 105752-11-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 105752-11-2, name is 3-Amino-4-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

A reselable pressure tube was charged with 4-iodopyridin-3 -amine (2.4 g, 10.9 mmol), 4-(triethylsilyl)but-3-yn-ol (5.0 g, 27.3 mmol), lithium chloride (0.46 g, 42.0 mmol), sodium carbonate (2.31 g, 21.8 mmol) and 1,1 ‘- bis(diphenylphosphino)ferrocenopalladium(II) dichloride, toluene (0.45 g, 0.55 mmol), the tube was sealed and heated on a 100 C oil bath for ~20h. The reaction mixture was cooled to ambient temperature, diluted with EtOAc (75 mL) and ether (75 mL). Water (150 mL) was added and the biphasic mixture was filtered through celite. The filtrate was transferred to a separatory funnel and the phases were separated and the aqueous fraction extracted twice more with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude was purified by silica gel chromatography, eluting with 2-20% (9: 1 MeOH/NH4OH)/chloroform, affording 2- (2-(triethylsilyl)-lH-pyrrolo[2,3-c]pyridin-3-yl)ethanol (2.45 g, 81% yield). LCMS method A: retention time = 3.44 min, M+H = 277.25. 1H NMR (400MHz, CHLOROFORM-d) delta = 8.79 (s, 1H), 8.65 – 8.47 (m, 1H), 8.22 (d, J=5.5 Hz, 1H), 7.56 (d, J=5.3 Hz, 1H), 3.91 (t, J=6.9 Hz, 2H), 3.13 (t, J=6.9 Hz, 2H), 1.82 (br. s, 1H), 1.12 – 0.90 (m, 15H).

According to the analysis of related databases, 105752-11-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MCDONALD, Ivar M.; ZUSI, F. Christopher; OLSON, Richard E.; WO2015/191403; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem