Category: 1227270-32-7

Related Products of 1227270-32-7, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1227270-32-7, name is 2-Iodo-1H-pyrrolo[2,3-b]pyridine, molecular formula is C7H5IN2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Compound 2 (1.5 g, 6.15 mmol), copper iodide (118 mg, 0.62 mmol), bis(triphenylphosphine)palladium(II) dichloride (217 mg, 0.31 mmol), triethylamine (1.28 mL, 9.23 mmol), ethynyl(trimethyl)silane (1.30 mL, 9.23 mmol) and THF (35 mL) were introduced in an oven dried round bottom flask under inert atmosphere. The mixture was stirred at room temperature for 20 h. The reaction mixture was diluted with EtOAc and filtered on Dicalite. The filtrate was washed with water and a saturated solution of sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel column, cyclohexane/EtOAc 7:3, to give 1.099 g of the clean expected product as a beige solid in 84% yield. 4.2.9 2-((Trimethylsilyl)ethynyl)-1H-pyrrolo[2,3-b]pyridine (3c) The derivative 3c was synthesized following the general procedure for the Sonogashira coupling reaction from 7. The crude product was purified by chromatography on silica gel column, cyclohexane/EtOAc 98:2, to give 381 mg of the clean expected product as an orange solid in 86% yield. 1H NMR (300 MHz, DMSO-d6) delta (ppm): 12.14 (brs, 1H), 8.27 (dd, J = 1.5, 4.7 Hz, 1H), 7.93 (ddd, J = 0.6, 1.5, 7.9 Hz, 1H), 7.09 (dd, J = 4.7, 7.9 Hz, 1H), 6.77 (sd, J = 2.0 Hz, 1H), 0.27 (s, 9H). 13C NMR (75 MHz, DMSO-d6) delta (ppm): 148.5, 145.2, 129.1, 119.6, 119.2, 116.9, 107.4, 99.2, 98.0, 0.2 (3C).

According to the analysis of related databases, 1227270-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Baltus, Christine B.; Jorda, Radek; Marot, Christophe; Berka, Karel; Bazgier, Vaclav; Kry?tof, Vladimir; Prie, Gildas; Viaud-Massuard, Marie-Claude; European Journal of Medicinal Chemistry; vol. 108; (2016); p. 701 – 719;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

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