Electric Literature of 1227270-32-7, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1227270-32-7 as follows.
In a vial, 2-iodo-1H-pyrrolo[2,3-b] pyridine 18a (200 mg, 0.82 mmol, 1 eq.) was dissolved in 8 ml of acetonitrile. Then 0.4 ml of acetic acid followed by 182 mg of Eschenmoser’s salt (0.98 mmol, 1.2 eq.) were added. After sealing the vial, the reaction mixture is stirred for 20 h at room temperature. 15 ml of a 2M solution of potassium hydroxide is added slowly and then the organic phase was extracted with ethyl acetate (3×20 ml). The organic phases are combined and then dried over MgSO4, filtered through cotton and evaporated to dryness. Finally, the crude is triturated with pentane and then vacuum filtered to obtain compound 174 (190 mg, 77%) as a yellow solid. Rf=0.10 (methanol/dichloromethane=2/98) mp=142-144 C. IR (v, cm-1, neat) 2957, 2932, 2851, 2812, 2768, 1603, 1580, 1514, 1489, 1448, 1407, 1369, 1354, 1328, 1287, 1273, 1248, 1206, 1167, 1147, 1121, 1094, 1036, 1004, 978, 905, 842. 1H NMR (400 MHz, CDCl3, 20 C.) delta 13.08 (s1, 1H), 8.41 (dd, J=4.9, 1.4 Hz, 1H), 8.09 (dd, J=7.9, 1.4 Hz, 1H), 7.11 (dd, J=7.9, 4.8 Hz, 1H), 3.60 (s 2H), 2.33 (s, 6H). 13C NMR (101 MHz, CDCl3, 20 C.) delta 151.0 (Cq), 142.0 (CH), 127.4 (CH), 121.3 (Cq), 116.7 (Cq), 115.8 (CH), 82.9 (Cq) 56.1 (CH2), 45.4 (2×CH3). HRMS (+ESI) calculated for C10H12IN3 (M+H+): 302.0148, found: 302.0148.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1227270-32-7, its application will become more common.
Reference:
Patent; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE D’ ORLEANS; UNIVERSITE FRANCOIS RABELAIS DE TOURS; CENTRE HOSPITALIER REGIONAL UNIVERSITAIRE DE TOURS; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE; ROUTIER, Sylvain; SUZENET, Franck; CHALON, Sylvie; BURON, Frederic; VERCOUILLIE, Johnny; MELKI, Ronald; BOIARYNA, Liliana; GUILLOTEAU, Denis; PIERI, Laura Ronald; (144 pag.)US2019/211011; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem