7205-46-1 | Pyridine-derivatives

A new synthetic route of 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7205-46-1, its application will become more common.

Electric Literature of 7205-46-1 ,Some common heterocyclic compound, 7205-46-1, molecular formula is C7H6ClN3, 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.

4-Amino-3-ethyl-phenol (100 mg, 0.73 mmol, 1.0 equiv), 6-Chloro-l -methyl- 1H- imidazo[4,5-c]-pyridine (134 mg, 0.80 mmol, 1.1 equiv), Cs2C03 (714 mg, 2.19 mmol, 3.0 equiv), BetaGammaNuAlphaRho (46 mg, 0.07 mmol, 0.1 equiv), and Pd2(dba)3 (33 mg, 0.04 mmol, 0.05 equiv) were dissolved in dry dioxane (5 mL) under N2 atmosphere. The mixture was sonicated for 5 mn under N2 flow and then re fluxed for 20h. Full conversion was observed by LCMS. It was then cooled down and concentrated to dryness, diluted in DCM and washed with water (3x 20 mL). The aqueous layer was extracted with DCM (3x 30 mL) and the combined organic layer was dried over Na2SO i, filtered and concentrated to dryness. Purification was performed by column chromatography using the following eluant: EtOAc/Petroleum Ether (1 : 1) to EtOAc (over 5 CV), MeOH/EtOAc (1 : 19) (10 CV), MeOH/EtOAc (1 :9) (10 CV) to afford the desired compound

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,7205-46-1, its application will become more common.

Reference:
Patent; GALAPAGOS NV; MENET, Christel Jeanne Marie; SCHMITT, Benoit Antoine; GENEY, Raphael Jean Joel; DOYLE, Kevin James; PEACH, Joanne; PALMER, Nicholas John; JONES, Graham Peter; HARDY, David; DUFFY, James Edward Stewart; WO2013/117645; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New learning discoveries about 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 7205-46-1, 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine, other downstream synthetic routes, hurry up and to see.

Application of 7205-46-1, Adding some certain compound to certain chemical reactions, such as: 7205-46-1, name is 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine,molecular formula is C7H6ClN3, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7205-46-1.

6-Chloro-l-methyl-lH-imidazo[4,5-c]pyridine (2.52 g, 0.015 mol) was stirred with 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.86 g, 0.0015 mol), sodium-tert-butoxide (2.16 g, 0.0225 mol) and 4-(4-methoxybenzyloxy)-2-methylaniline (3.68 g, 0.015 mol) in dry dioxane (50 mL) under N2 (g) for 30 minutes. Tris(dibenzylideneacetone)dipalladium(0) (0.68 g, 0.00075 mol) was added and the mixture was stirred at 100C for 4.5 h. The mixture was concentrated in vacuo and the residue was treated with water (50 mL) and extracted into EtOAc (2 x 300 mL). The combined extracts were washed with brine, dried (MgSO i), filtered and concentrated in vacuo to give a solid which was recrystalised from isopropanol to give the desired compound. [00306] NMR delta (ppm)(DMSO-d6): 8.43 (1 Eta, d, ArH), 7.98 (1 H, s, NH), 7.75 (1 H, s, ArH), 7.39 (2 H, d, ArH), 7.27 (1 H, d, ArH), 7.00-6.90 (3 H, m, ArH), 6.82 (1 H, dd, ArH), 6.38 (1 H, d, ArH), 5.00 (2 H, s, CH), 3.77 (3 H, s, CH3), 3.64 (3 H, s, CH3), 2.17 (3 H, s, CH3).

Reference:
Patent; GALAPAGOS NV; MENET, Christel; SCHMITT, Benoit; GENEY, Raphael; DOYLE, Kevin; PEACH, Joanne; PALMER, Nicholas; JONES, Graham; HARDY, David; DUFFY, James; WO2013/117649; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New downstream synthetic route of 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 7205-46-1, 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine.

Reference of 7205-46-1, 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. 7205-46-1, name is 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine, molecular formula is C7H6ClN3, 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.

A mixture of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.08 g), 6-chloro-l-methyl- lH-imidazo[4,5-c]pyridine (0.23 g, 0.0014 mol), 3-amino-4-ethyl-N,N-dimethylbenzamide (0.27 g, 0.0014 mol) and sodium tert-butoxide (0.20 g, 0.0021 mol) in 1,4-dioxane (15 mL) was stirred under N2 for 20 min. Tris(dibenzylideneacetone)dipalladium(0) (0.06 g) was added and the mixture was stirred at 100C for 7 h. The reaction mixture was concentrated in vacuo and the residue was treated with water and extracted into EtOAc. The organics were washed with brine, dried (MgSO i) and concentrated in vacuo to give the desired compound. For analytical purpose, a 60 mg sample was further purified by preparative HPLC to give the desired compound. [00324] NMR delta (ppm)(CHCl3-d): 8.69 (1 H, d, ArH), 7.71 (1 H, s, ArH), 7.52 (1 H, d, ArH), 7.32 (1 H, m, ArH), 7.16 (1 H, dd, ArH), 6.63 (1 H, d, ArH), 6.36 (1 H, s, NH), 3.68 (3 H, s, CH3), 3.09 (3 H, s, CH3), 3.03 (3 H, s, CH3), 2.69 (2 H, q, CH2), 1.24 (3 H, t, CH3). [00325] LCMS (lOcm ESCI Formic MeCN) tR 2.21 (min) m/z 324 (MH+).

Analyzing the synthesis route of 6-Chloro-1-methyl-1H-imidazo[4,5-c]pyridine

Reference of 7205-46-1 ,Some common heterocyclic compound, 7205-46-1, molecular formula is C7H6ClN3, 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 degassed mixture of the amine (1 eq, 28 mg), 6-chloro-l-methyl-lH-imidazo[4,5- c]pyridine (1 eq, 27 mg), CS2CO3 (2.5 eq, 132 mg), Xphos (0.3 eq, 23 mg) and Pd2(dba)3 (0.1 eq, 15 mg) in dry DMF (1 mL) was heated at 110C for 18 h. Water was added and the reaction mixture was extracted with EtOAc (3 x). The combined organics were dried, concentrated and the residue was purified by silica chromatography (MeOH/EtOAc; 0:100 to 10:90) to give the desired compound