Month: December 2020

A common compound: 120781-02-4, name is Methyl 2-bromo-1-methyl-1H-imidazole-5-carboxylate, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 120781-02-4

[0277] In a microwave tube was placed N,N-bis(4-methoxybenzyl)-4-((3-phenyl-1H- pyrazol-4-yl)methyl)benzenesulfonamide (138 mg, 0.25 mmol), methyl 2-bromo-i-methyl- 1 H-imidazole-5-carboxylate (54.8 mg, 0.25 mmol), (1 S,2S)-Ni ,N2-dimethylcyclohexane- 1,2- diamine (14.22 mg, 0.100 mmol), Cul (9.52 mg, 0.050 mmol), and Phosphoric acid, potassium salt (159 mg, 0.750 mmol). The air was removed and re-filled with N2 (3 times). Then Toluene (2 ml) was added and the mixture was stirred at 110 C for overnight. After cooling to rt, the mixture was dilute with EtOAc (3 mL) and filtered through celite and eluted with EtOAc. The filtrate was concentrated and the mixture was purified by silica gel chromatography using 10-25% EtOAc/hexane as the eluent to give methyl 2-(4-(4-(N,N- bis(4-methoxybenzyl)sulfamoyl)benzyl)-3 -phenyl- 1 H-pyrazol- 1 -yl)- i-methyl- 1H-imidazole- 5-carboxylate (57 mg, 0.082 mmol, 33.0 % yield). MS (M+H) = 692.

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, 120781-02-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE UNITED STATES OF AMERICA AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; VANDERBILT UNIVERSITY; MALONEY, David J.; JADHAV, Ajit; BANTUKALLU, Ganesha Rai; BRIMACOMBE, Kyle Ryan; MOTT, Bryan T.; YANG, Shyh Ming; URBAN, Daniel Jason; HU, Xin; SIMEONOV, Anton; KOUZNETSOVA, Jennifer L.; WATERSON, Alex Gregory; SULIKOWSKI, Gary Allen; KIM, Kwangho; CHRISTOV, Plamen; JANA, Somnath; (387 pag.)WO2016/109559; (2016); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

29043-48-9,Some common heterocyclic compound, 29043-48-9, name is 2-Methyl-1H-benzoimidazol-5-ylamine, molecular formula is C8H9N3, 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.

General procedure: A mixture of compound II-1, II-2 or II-3 (2 mmol),SnCl2¡¤2H2O (10 mmol) in EtOAc (15 mL) was refluxed for12 h. When the reaction was complete according to TLCanalysis, the resulting reaction mixture was cooled to room temperature. Subsequently, the reaction mixture wasadjusted to pH 8-9 with saturated aq. NaHCO3 (50 mL).Then the mixture was extracted with EtOAc (2 ¡Á 150 mL).The combined organic phase was washed with brine (200mL), dried over anhydrous Na2SO4, and concentrated toafford compounds III-1, III-2 or III-3, which were useddirectly for the next step without further purification. To amixture of 5-amino-1H-benzimidazole (III-1, III-2 or III-3,2 mmol), water (5 mL) and concentrated HCl (12 mol/L,0.51 mL) at 0C, a solution of sodium nitrite (NaNO2, 2.1mmol) in water (10 mL) was added dropwise whilemaintaining the temperature below 5C. After stirring for 20min, a solution of diazonium chloride was prepared.Subsequently, a solution of diazonium chloride was addedgradually to a mixture of phenols (IV-1-IV-10, 2 mmol),sodium hydroxide (NaOH, 2 mmol), ethanol (15 mL) andwater (25 mL) at 0-5C. After the addition of the abovediazonium solution, the mixture was continued to stir for 3-6h until a lot of precipitate was produced. The solid wascollected, washed with water (3¡Á10 mL), dried and purifiedby PTLC to give the target products V-1~V-28.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methyl-1H-benzoimidazol-5-ylamine, its application will become more common.

Reference:
Article; Ke, Yazhen; Zhi, Xiaoyan; Yu, Xiang; Ding, Guodong; Yang, Chun; Xu, Hui; Combinatorial Chemistry and High Throughput Screening; vol. 17; 1; (2014); p. 89 – 95;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2625-49-2, A common heterocyclic compound, 2625-49-2, name is 2-(1-Methyl-1H-imidazol-4-yl)acetic acid, molecular formula is C6H8N2O2, 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.

General procedure: To a mixture of 2-amino-5-(4-methylphenyl) thiophene-3-carboxamide 1a (0.25 g, 0.107 mol) and 4-benzyloxy benzoic acid 4a (0.319 g, 0.140 mol) in anhydrous chloroform (4 ml) was added triethylamine (0.32 g, 0.323 mol) and phosphonic acid cyclic anhydride (1.02 g, 0.323 mol). The reaction mixture was irradiated at 120 C in a microwave initiator for a given period of time (Table 1, entry 1). Once the substrate was completely consumed as monitored by TLC, the brown reaction mixture was cooled and poured into ice-cold water (10 ml). The product was extracted with ethyl acetate (2 ¡Á 25 ml) and the combined organic phase was washed with water, brine solution and dried over anhydrous sodium sulfite. The solvent was removed under vacuum and the brown residue was passed through a small plug of silica gel using petroleum ether/ethyl acetate (9/1) to afford 429 mg (94%) of 2a as a yellow solid.

The synthetic route of 2625-49-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Poojari, Subba; Parameswar Naik; Krishnamurthy; Tetrahedron Letters; vol. 53; 35; (2012); p. 4639 – 4643;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 24134-09-6, name is 5-Bromo-1,2-dimethyl-1H-imidazole, molecular formula is C5H7BrN2, 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. 24134-09-6.

Preparation 95: 4-(1 ,2-Dimethyl-1 H-imidazol-5-yl)-2-methoxyaniline; [00265] To a microwave vial was added 5-bromo-1 ,2-dimethyl-1 /-/-imidazole (230mg, 1 .31 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (393mg, 1 .58mmol), Pd(PPh3)4 (152mg, 0.13mmol), CsF (599mg, 3.94mmol) and DME/MeOH 3/1 (4ml_). The mixture was heated in a microwave at 150C for 1 hour. The reaction mixture was then filtered and concentrated onto silica gel and purified by Biotage silica gel column chromatography eluting with (EtOAc/MeOH 100/0 to 96/4) to give the title product as a light brown oil (120mg, 42 %). 1 H NMR (500 MHz, CDCI3): delta 2.43 (s, 3H), 3.48 (s, 3H), 3.87 (s, 3H), 6.73-6.78 (m, 3H), 6.87 (s, 1 H). LC (Method A)-MS (ESI, m/z) tR 0.49 min, 218 [(M+H+), 100%].

The synthetic route of 5-Bromo-1,2-dimethyl-1H-imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Adding a certain compound to certain chemical reactions, such as: 5955-72-6, name is 2-Chloro-6-nitro-1H-benzo[d]imidazole, belongs to imidazoles-derivatives compound, 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 5955-72-6, 5955-72-6

To a suspension of 3.952 g (20 mmole) of 19 in 100 mL of 1,2-dichloroethane, was added 5 mL (20 mmole) of BSA. The reaction mixture was stirred at 75 C. for 15 min to give a clear solution. This solution was cooled to ~ 20 C. and treated with 7.0 g (22 mmole) of 1,2,3,5-tetra-O-acetyl-b-D-ribofuranose and 4.638 mL (24 mmole) of TMSOTf at room temperature for 2 h. The reaction mixture was diluted with 200 mL of CHCl3. The CHCl3 solution was washed with sat. NaHCO3 solution (200 mL*2), sat. NaCl solution (200 mL), dried (Na2 SO4), and evaporated. The residue was chromatographed on a silica column (5*35 cm, eluted with CHCl3 and 0.5% MeOH/CHCl3). Evaporation of the appropriate fractions gave 6.50 g (71% one spot on TLC) of 74 and 75 as a white foam. Fractional recrystallization of this foam (5 times from MeOH) give 1.59 g (17%) of the pure 6-nitro isomer 75. MP 127-129 C. MS (EI) m/e 455.0750 (2%, M+ =455.0732). 1 H NMR (DMSO-d6): d 8.68 (d, 1, 7-H, J7-5 =2.0 Hz), 8.21 (dd, 1, 5-H, J5-4 =9.0 Hz), 7.88 (d, 1, 4-H), 6.41 (d, 1, 1′-H, J1′-2′ =7.0 Hz), 5.58 (t, 1, 2′-H, J2′-3′ =7.0 Hz), 5.45 (dd, 1, 3′-H, J3′-4′ =4.0 Hz), 4.50, 4.40 (2*m, 3, 4′-H and 5′-H), 2.15, 2.12, 2.03 (3*s,9, 3*Ac). 13 C NMR (DMSO-d6): d 170.12, 169.49, 169.25 (3*OCOCH3), 145.60 (C3a), 143.96 (C2), 143.65 (C6), 132.46 (C7a), 119.65 (C4), 118.92 (C5), 108.47 (C7), 86.96 (C1′), 79.67 (C4′). 71.12 (C2′), 68.75 (C3′), 62.56 (C5′), 20.39, 20.31, 20.03 (3*OCOCH3).

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, 2-Chloro-6-nitro-1H-benzo[d]imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Regents of the University of Michigan; US5574058; (1996); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2620-76-0,Some common heterocyclic compound, 2620-76-0, name is 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, molecular formula is C19H13BrN2, 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.

Example 1.1.3bis(pinacolate)diborane81%[0044] l-phenyl-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-lH- benzo[d]imidazole (3): A mixture of Compound 2 (0.70 g, 2 mmol), bis(pinacolate)diborane (0.533g, 2.1 mmol), bis(diphenylphosphino)ferrocene]dichloropalladium (Pd(dppf)Ci2) (0.060 g, 0.08 mmol) and anhydrous potassium acetate (KOAc) (0.393 g, 4mmol) in 1,4-dioxane (20 ml) was heated at 80 C under argon overnight. After cooling to RT, the whole was diluted with ethyl acetate (80 ml) then filtered. The solution was absorbed on silica gel, then purified by column chromatography (hexanes/ethyl acetate 5:1 to 3:1) to give a white solid 3 (0.64 g, in 81% yield)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromophenyl)-1-phenyl-1H-benzoimidazole, its application will become more common.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, Shijun; MA, Liping; MOCHIZUKI, Amane; LAI, Qianxi; KHAN, Sazzadur, Rahman; LI, Sheng; HARDING, Brett, T.; CHAE, Hyunsik; ROMERO, Rebecca; SISK, David, T.; WO2012/88294; (2012); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A common heterocyclic compound, 10394-38-4, name is 1-Methylbenzoimidazol-5-amine, molecular formula is C8H9N3, 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. 10394-38-4.

1-methyl-1H-benzo[d]imidazol-5-amine (100 mg, 0.67944 mmol),6-(4-((2,5-Dichloropyrimidin-4-yl)amino)piperidin-1-yl)nicotinonitrile (182 mg, 0.5212 mmol),Cs2CO3 (508.7 mg, 1.561 mmol),BINAP (34.6mg, 0.0556mmol) andPd(OAc) 2 (12.8 mg, 0.0570 mmol)The mixture was dissolved in 1,4-dioxane (10 mL). The reaction mixture is at 100 C,Stir for 4 hours in a nitrogen atmosphere.After the reaction was completed, it was concentrated under reduced pressure.The residue obtained was purified by silica gel column chromatography (DCM / MeOH (v/v) = 50/1)The title compound was obtained as a white solid (54.4mg, yield: 22.7%).

The synthetic route of 1-Methylbenzoimidazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Li Minxiong; Peng Ju; Li Xiaobo; Zhang Tao; Hu Haiyang; Chen Wuhong; Bai Changlin; Ke Donghua; Chen Peng; (217 pag.)CN109776522; (2019); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

256519-10-5, 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. 256519-10-5 name is 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one, This 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.

Preparation 47 2-Chloro 4-fluoro-1H-1,3-benzimidazole STR92 The title compound was prepared by the method of Preparation 25 from 4-fluoro-1,3-dihydro-2H-1,3-benzimidazole-2-one [see Preparation 46]. 1 H-NMR (d4-MeOH) delta: 7.32 (1H, d), 7.28 (1H, m), 7.00 (1H, t).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-1H-benzo[d]imidazol-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc; US6166011; (2000); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

2034-22-2, A common compound: 2034-22-2, name is 2,4,5-Tribromoimidazole, belongs to imidazoles-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

422.5 g of 2,4,5-tribromoimidazole, 1126.7 g of methanol were added to the reactor, 21.1 g of tetramethylammonium chloride was added, and 384.5 g of triphenylphosphine was added in portions while stirring.After the addition is complete, the reaction is incubated at 60-65C for about 1 hour until it reaches room temperature.Add ethyl acetate,While stirring, sodium bicarbonate solution was added dropwise, the layers were separated, and the organic layer was desolvated to precipitate a large amount of solids, which was then filtered and dried at room temperature to obtain 234.8 g of 4,5-dibromoimidazole in a yield of 75%.

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, 2,4,5-Tribromoimidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Dalian Qikai Pharmaceutical Technology Co., Ltd.; Jiang Bin; Jiang Dianping; Zhang Hongxue; (5 pag.)CN107827823; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

28890-99-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 28890-99-5, name is 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

250ml four bottles,In the atmosphere of nitrogen gas,0.01 mol of 5H-benzimidazol [1,2-a] benzimidazole was added,0.015 mol of 13- (4-bromophenyl) -10,10-dimethyl-10,13-dihydrobenzofuran [2,3-c] indole [1,2-g] carbazole,0.03 mol of sodium tert-butoxide,1 x 10-4 mol Pd2 (dba) 3,1 x 10-4 mol tri-tert-butylphosphine,150 ml of toluene,Heated to reflux for 24 hours,Sampling point plate, the reaction is complete, natural cooling, filtration, the filtrate steamed, silica gel column, the target product, purity 99.25, yield 49.00%.

The synthetic route of 5H-Benzo[d]benzo[4,5]imidazo[1,2-a]imidazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Sanyue Photoelectric Technology Co., Ltd.; Wang, Lichun; Li, Chong; Xu, Kai; Zhang, Zhaochao; Ye, Zhonghua; (39 pag.)CN106467552; (2017); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem