Category: 16681-59-7

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Bromo-1-methyl-1H-imidazole

General procedure: A mixture of 4-methyl-3-(4-(pyridin-2-ylmethoxy)benzamido)phenyl boronic acid (50 mg, 0.14 mmol), Cs2CO3 (135 mg, 0.41 mmol), Pd(PPh3)4(23.93 mg, 0.02 mmol) and 4-bromo-1H-imidazole (26 mg, 0.18 mmol) was purged with nitrogen before adding degassed dioxane (690 muL) and water (230 muL) and heating in a microwave for 40 min at 150 C. After cooling, the aqueous layer was removed with a pipette, and the organic layer was diluted with DMSO (1 mL) and filtered through a 0.2 mum filter. The filtrate was concentrated to a volume of 1 mL and purified by Gilson HPLC (20-75% MeCN/10 mM NH4OAc in water). The fractions were concentrated and lyophilized to yield the product (19 mg, 0.049 mmol, 35%). 1H NMR (DMSO-d6) delta ppm 12.11 (s, 1H), 9.76 (s, 1H), 8.59 (d, 1H), 7.97 (d, 2H), 7.85 (td, 1H), 7.70 (s, 1H), 7.67 (s, 1H), 7.56 (m, 2H), 7.36 (dd, 1H), 7.21 (d, 1H), 7.15 (d, 2H), 5.27 (s, 2H), 2.18 (s, 3H). LCMS (M+H) = 385.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Review; Yang, Bin; Hird, Alexander W.; Russell, Daniel John; Fauber, Benjamin P.; Dakin, Les A.; Zheng, Xiaolan; Su, Qibin; Godin, Robert; Brassil, Patrick; Devereaux, Erik; Janetka, James W.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4907 – 4911;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 16681-59-7

Step 2 To a 500 mL round flask was added N-methyl-2-bromoimidazole (6.50 g, 40 mmol),2,4-diflurophenylboronic acid (7.89g, 50 mmol), palladium(II) acetate (0.28 g, 1.25 mmol), triphenylphosphine (1.31 g, 5 mmol), sodium carbonate (14.31 g, 135 mmol), and 200 mL of DME and 100 mL of water. The reaction was heated to reflux and stirred under a nitrogen atmosphere for 12 hours. The mixture was extracted with ethyl acetate and further purified by a silica gel column. Distillation of the product at 150 C. gave N-methyl-2-(2,4-difluorophenyl)imidazole as a colorless oil (6.60 g, 85% yield), characterized by 1H-NMR and MS.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Lin, Chun; Ma, Bin; Knowles, David B.; Brooks, Jason; Kwong, Raymond; US2006/8670; (2006); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

These common heterocyclic compound, 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, 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. COA of Formula: C4H5BrN2

The 3-methyl-1-(1-methyl-1 H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid used in the method described above was prepared as follows: (i) To a stirred solution of 1 ,1-dimethylethyl 3-methyl-2-oxo-4- imidazolidinecarboxylate (0.200 g, 1.00 mmol) (prepared as described in step (iii) of Example 13, starting from (4S)-2-oxo-3-{[(phenylmethyl)oxy]carbonyl}-4- imidazolidinecarboxylic acid) and 2-bromo-1-methyl-1 H-imidazole (0.146 ml, 1.500 mmol) in 1 ,4-dioxane (8 ml) was added potassium phosphate (1.062 g, 5.00 mmol), copper(l) iodide (0.190 g, 1.000 mmol) and trans-N,N-dimethylcyclohexane-1 ,2- diamine (0.155 ml, 1.000 mmol) and the mixture heated at reflux under argon overnight. The mixture was cooled to room temperature and diluted with dichloromethane. The solid was filtered off, washed with dichloromethane and the filtrate reduced under vacuum. The residue was re-dissolved in dichloromethane and washed with 0.880 ammonia solution (x2), water then brine and passed through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by Flashmaster automated silica gel chromatography eluting with 0-10% methanol in dichloromethane to give 1 ,1-dimethylethyl 3-methyl-1-(1-methyl-1 H- imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylate (145 mg, 37.8 % yield). LC/MS[M+H]+ = 281.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/119825; (2008); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 16681-59-7, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, This compound has unique chemical properties. The synthetic route is as follows.

Compound A1 (16.1 g, 100 mmol) was sequentially added to the flask under argon gas protection.Compound B1 (12.3 g, 105 mmol), Pd(PPh3) 4 (2.31 g, 2 mmol),Toluene (300 ml), aqueous sodium carbonate (2M, 150 ml),Stir under reflux for 8 hours. After cooling the above reaction solution to room temperature,Extract with toluene and combine the organic phases.The organic phase is washed with saturated brine, and the organic phase is dried and concentrated.Column chromatography was carried out using silica gel as a stationary phase to give Compound D1.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1-methyl-1H-imidazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Han Chunxue; Sun Jing; (31 pag.)CN108892690; (2018); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-1-methyl-1H-imidazole

A solution of 1 mmol (0.167 g) of carbazole, 2 mmol (0.322 g) of 2-bromo-N-methyl-imidazole, benzotriazole 40 mol% (0.046 g) 20 mmol% (0.038 g) of copper iodide and 1.4 mmol (0.157 g) of potassium tertiary-butoxide were stirred in 6 mL of dimethylsulfoxide at 135C for 48 hours. The reaction mixture was allowed to cool and then water was added and extracted with ethyl acetate. The ethyl acetate extract was dried over magnesium sulfate and then distilled under reduced pressure. The resulting brown solid was purified by silica column chromatography (using ethyl acetate and hexane). Finally, a colorless solid ligand 12 was obtained. The yield of the ligand 12 was 40%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Samsung Electronics Co., Ltd.; Samsung SD I Co., Ltd.; Das, Rupa Sri Rajini; Lee, Gang Mun; Noh, Chang Ho; Bae, Hay Jin; Rai, Birendra Kumar; Kravtsuk, Dmitry; (49 pag.)KR2016/12890; (2016); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-1-methyl-1H-imidazole

Compound 7a (100 mg, 268 mumol), 2-bromo-1-methyl-1H-imidazole (65 mg, 402 mumol), triethylamine (73 muL, 541 mumol), and dimethylformamide (2 mL) were combined in a sealed tube. The mixture was sparged for 2 minutes with nitrogen, and bis(triphenylphosphine) palladium dichloride (19 mg, 27 mumol) was added followed by copper iodide (10 mg, 53 mumol). The mixture was sparged again with nitrogen and stirred for 20 minutes at 70 C under microwave irradiation. The reaction was diluted with ethyl acetate (50 mL), washed with a saturated solution of ammonium chloride (50 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure and purified by flash chromatography on silica gel (DCM/MeOH: 96/4) to give compound 83 (62 mg, 137 mumol, 51%).1H NMR (400 MHz, Acetone- d6) delta 9.51 (s, 1H), 8.35 (s, 1H), 7.99 (ddd, J = 13.2, 7.4, 2.6 Hz, 1H), 7.57- 7.48 (m, 1H), 7.34 (dt, J = 10.5, 9.0 Hz, 1H), 7.14 (d, J = 1.2 Hz, 1H), 6.92 (d, J = 1.2 Hz, 1H), 4.46 (d, J = 5.8 Hz, 2H), 3.75 (s, 3H), 3.70 (s, 3H), 2.46 (s, 3H), 2.32 (s, 3H). 19F NMR (377 MHz, Acetone-d6) delta -139.91- -140.01 (dt, J = 22.1, 11.6 Hz), -147.12- – 147.23 (dt, J = 20.5, 10.4 Hz). MS (ESI): m/z [M+H]+ calcd for C23H22F2N5O3 : 454.4, found: 454.4

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; EMORY UNIVERSITY; SCHINAZI, Raymond F.; BOUCLE, Sebastien; AMBLARD, Franck; SARI, Ozkan; BASSIT, Leda; (169 pag.)WO2017/156255; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-1-methyl-1H-imidazole

Compound 7a (100 mg, 268 mumol), 2-bromo-1-methyl-1H-imidazole (65 mg, 402 mumol), triethylamine (73 muL, 541 mumol), and dimethylformamide (2 mL) were combined in a sealed tube. The mixture was sparged for 2 minutes with nitrogen, and bis(triphenylphosphine) palladium dichloride (19 mg, 27 mumol) was added followed by copper iodide (10 mg, 53 mumol). The mixture was sparged again with nitrogen and stirred for 20 minutes at 70 C under microwave irradiation. The reaction was diluted with ethyl acetate (50 mL), washed with a saturated solution of ammonium chloride (50 mL). The organic phase was dried over sodium sulfate and concentrated under reduced pressure and purified by flash chromatography on silica gel (DCM/MeOH: 96/4) to give compound 83 (62 mg, 137 mumol, 51%).1H NMR (400 MHz, Acetone- d6) delta 9.51 (s, 1H), 8.35 (s, 1H), 7.99 (ddd, J = 13.2, 7.4, 2.6 Hz, 1H), 7.57- 7.48 (m, 1H), 7.34 (dt, J = 10.5, 9.0 Hz, 1H), 7.14 (d, J = 1.2 Hz, 1H), 6.92 (d, J = 1.2 Hz, 1H), 4.46 (d, J = 5.8 Hz, 2H), 3.75 (s, 3H), 3.70 (s, 3H), 2.46 (s, 3H), 2.32 (s, 3H). 19F NMR (377 MHz, Acetone-d6) delta -139.91- -140.01 (dt, J = 22.1, 11.6 Hz), -147.12- – 147.23 (dt, J = 20.5, 10.4 Hz). MS (ESI): m/z [M+H]+ calcd for C23H22F2N5O3 : 454.4, found: 454.4

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; EMORY UNIVERSITY; SCHINAZI, Raymond F.; BOUCLE, Sebastien; AMBLARD, Franck; SARI, Ozkan; BASSIT, Leda; (169 pag.)WO2017/156255; (2017); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 16681-59-7, 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. 16681-59-7 name is 2-Bromo-1-methyl-1H-imidazole, 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.

General procedure: Reactions were carried out in a Bohdan XT 24 position block using the appropriate halide indicated.2M Sodium carbonate (0.680 mL, 1.36 mmol) was added to a stirred mixture of 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine (10, 151 mg, 0.62 mmol), the appropriate halide (0.74 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (Pd(Amphos)Cl2) (26.3 mg, 0.04 mmol) in DME (4 mL) under nitrogen. The resulting mixture was stirred at 80 C for 4 h, allowed to cool, diluted with water (10 mL), extracted with EtOAc (2×25 mL) and the organic layer was evaporated to afford crude products. Unless otherwise stated the crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5 mu silica, 19 mm diameter, 100 mm length, 5-95% MeCN/1% NH3 in H2O).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-methyl-1H-imidazole, and friends who are interested can also refer to it.

Reference:
Article; Bethel, Paul A.; Campbell, Andrew D.; Goldberg, Frederick W.; Kemmitt, Paul D.; Lamont, Gillian M.; Suleman, Abid; Tetrahedron; vol. 68; 27-28; (2012); p. 5434 – 5444;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 16681-59-7, 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 16681-59-7 as follows.

2-Bromo-l -methyl- 1H- imidazole (47 mu-, 0.48 mmol) was dissolved in diethyl ether (2 mL) and cooled to -75C under argon. Butyl lithium (2.5 M in hexanes: 192 (uL, 0.48 mmol) was added dropwise and the mixture stirred at -75C for 1 hour. A solution of (R)-l-(4- fluorophenyl)-6-((4-(trifluoromemyl)phenyl)sulfonyl)-4,4a,5,6,7,8-hexahydro-lH-pyra.zolo[3,4- g]isoqumoline~4a~carbaldehyde (252 mg, 0.5 mmol) in diethyl ether (2 mL) was added dropwise The reaction mixture was stirred for 16 hours whilst warming slowly to room temperature. The reaction mixture was cooled and treated with water (10 mL) and the phases separated. The organic phase was extracted with further diethyl ether (x2) followed by diehloromethane (x2). The combined organic phases were dried over sodium sulfate, the solids were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient: 17.5 to 25% acetone in cyelohexane) to afford (R)-(l-(4-fluorophenyl)-6-((4-(Mflu^ pyrazolo[3,4-g]isQquinoim-4a-yi)(l as a white powder (82 mg) LCMS (Method A, ESI): RT 2.74 min, m+H = 588.1

According to the analysis of related databases, 16681-59-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORCEPT THERAPEUTICS, INC.; HUNT, Hazel; JOHNSON, Tony; RAY, Nicholas; WALTERS, Iain; WO2013/177559; (2013); A2;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 16681-59-7, 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. 16681-59-7, name is 2-Bromo-1-methyl-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 62 (METHOD O); 6,6-Dimethyl-2-[6-(l-methyl-lH-imidazol-2-yl)-2,3-dihvdrobenzo[l,41oxazin-4-yll-6,7- dihydro [ 1 ,31 thiazolo [ 5 A-c] p yridin-4( 5H)-one; A mixture of Intermediate 66 (0.050 g, 0.14 mmol), l-methyl-2-bromoimidazole (0.067 g, 0.4 mmol), tetra-n-butylammonium bromide (0.135 g, 0.4 mmol), Na2CO3 (0.045 g, 0.4 mmol), tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) and water (1 mL) in TetaF (3 mL) was heated to 1400C under microwave irradiation for 20 minutes. Additional portions of l-methyl-2-bromoimidazole (0.033 g, 0.2 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.016 g, 0.014 mmol) were added, and heating continued for a further 40 minutes. After cooling to r.t., the reaction mixture was concentrated in vacuo, and the residue partitioned between DCM (50 mL) and water (50 mL). The organic fraction was washed with water (50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by preparative etaPLC (Method 6) to give the title compound (0.002 g, 4%) as a white solid. deltaeta (CDCl3) 8.18 (IH, d, J 1.9 Hz), 7.33 (IH, dd, J8.5 and J 1.9 Hz), 7.02 (IH, d, J 1.3 Hz), 6.98 (IH, d, J 8.5 Hz), 6.89 (IH, d, J 1.1 Hz), 5.10 (IH, br. s), 4.36-4.29 (2H, m), 4.12-4.04 (2H, m), 3.74 (3H, s), 2.80 (2H, s), 1.32 (6H, s). LCMS (ES+) 396.0 (M+H)+, RT 1.66 minutes (Method I).

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

Reference:
Patent; UCB PHARMA S.A.; WO2008/1076; (2008); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem