Tag: M.W=200-300

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. 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H3Br2F

Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.

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; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason Allan; PHADKE, Avinash S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (358 pag.)WO2017/35411; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 40422-70-6, These common heterocyclic compound, 40422-70-6, name is 1-Bromo-3-(2-bromoethyl)benzene, 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: Table 3 is a parameter table. The starting material “parameter 1” was added into a flask at room temperature under N2, and then the “parameter 2” mL IPA and “parameter 3” were added thereinto. The starting material was dissolved at “parameter 4” C. The appearances of reaction solution were “parameter 5” and “parameter 7” in about “parameter 6” minutes, and then the solution was heated at 110~120C for “parameter 8” hours and concentrated in room temperature. The “parameter 9” mL MeOH was added and the resulting mixture was stirred for “parameter 10” minutes. To the solution, which is “parameter 1 1” in a ice-bath, NaBH4(s) “parameter 12” was added slowly under N 2 and stirred for “parameter 13” minutes. The solution, which is “parameter 14,” was added with “parameter 15” mL H2O and extracted with “parameter 16” mL CHC13. The organic layer was added with MgS04 for drying, stirred for “parameter 17” minutes, filtered, and concentrated to obtain “parameter 18”. The “parameter 20” was afforded after flash column chromatography (silica gel, “parameter 19”).

Statistics shows that 1-Bromo-3-(2-bromoethyl)benzene is playing an increasingly important role. we look forward to future research findings about 40422-70-6.

Reference:
Patent; YU, Linda Chia-Hui; HSIN, Ling-Wei; LEE, Tsung-Chun; (0 pag.)WO2018/157233; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 6698-13-1, name is 4-Bromo-1,3-benzodioxole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-1,3-benzodioxole

To a stirred solution of 4-bromo-1,3-benzodioxole (65 mg, 0.323 mmol, 1 eq.) and chloro(di-2-norbornylphosphino)(2’dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (18 mg) in anhydrous dioxane (3 mL) under nitrogen2 is added a dioxane (3 mL) solution of [3-(tert-butyl-diphenyl-silanyloxy)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-pyridin-3-yl-amine (196 mg, 0.356 mmol, 1.1 eq) followed by 2M aqueous K3PO4 (0.35 mL, 0.7 mmol). The mixture is heated to 100 C. in a sealed tube overnight. The reaction mixture was returned to ambient temperature, and diluted with methylene chloride. The organic phase washed with brine, dried over MgSO4, filtered and concentrated to a dark brown oil. Flash chromatography (1% MeOH/methylene chloride) gave 117 mg of 3-benzo[1,3]dioxol-4-yl-5-(tert-butyl-diphenyl-silanyloxy)-phenyl]-pyridin-3-yl-amine as a beige solid.

According to the analysis of related databases, 6698-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 261723-28-8, name is (3-Bromo-2-fluorophenyl)methanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 261723-28-8

TEA (2.11 g, 20.88 mmol) and B0C2O (1.67 g, 7.66 mmol) were added to a solution of Compound BDl l-4 (1.42 g, 6.96 mmol) in DCM (30.00 mL). The mixture was stirred at 15C for 12 hours. LCMS showed the production of BD11-5. The reaction was concentrated to give a residue. The residue was purified by column chromatography (S1O2, petroleum ether: ethyl acetate mixture with a ratio of 30: 1 to 10: 1) to afford Compound BD11-5 (2.00 g, crude) as a white solid.

The synthetic route of 261723-28-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE BROAD INSTITUTE, INC.; VACCA, Joseph, P.; (103 pag.)WO2018/75871; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 41825-73-4, name is 2-Bromo-4,6-dimethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Bromo-4,6-dimethylaniline

a) Synthesis of A/-(2-bromo-4,6-dirnethyl-phenyl)-iH-benzimidazol-2-amine 2-Chlorobenzimidazole (6.9 g, 45.4 mmol) and 2-bromo-4,6-dimethylaniline (10.0 g, 50.0 mmol) are dissolved in NMP (23 imL) at 20C. Methanesulfonic acid (4.8 g, 50.0 mmol) is added dropwise over ca. 0.5 h. The resulting suspension is heated to 100C and stirred until complete conversion of 2-chlorobenzimidazole. The reaction mixture is then cooled to 20C, diluted with water (14 ml.) and neutralized with 30 w-% aqueous sodium hydroxide (12.7 g, 95.3 mmol). The precipitated reaction product is isolated by filtration, washed with water and dried under vacuum at 90C. Crude A/-(2-bromo-4,6-dimethyl-phenyl)- iH- benzimidazol-2-amine (10.3 g, 72%) is obtained as an off-white amorphous solid, which was further purified by recrystallization from methanol. 1 H-NMR (DMSO-d6): delta = 2.21 (s, 3H), 2.31 (s, 3H), 6.83-6.95 (m, 2H), 7.06-7.18 (m, 3H), 7.39 (brs, 1 H), 8.58 (brs, 1 H), 10.75 (brs, 1 H) ppm.

The synthetic route of 41825-73-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UDC IRELAND LIMITED; GREEF, DE, Michiel; PETER, Bernd; STUMPF, Ruediger; (36 pag.)WO2017/17096; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 376646-62-7, name is (4-Bromo-2-methylphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (4-Bromo-2-methylphenyl)methanamine

[0618j To a solution of 1-tert-Butyl-1H-pyrazole-4-carboxylic acid (1.4 g, 8.4 mmol) in DMF (20 mL) was added HATU (3.5 g, 9.2 mmol) and DIEA (4.4 mL, 25 mmol). The mixture was stirred at rt for 5 mm, followed by the addition of (4-bromo-2-methylphenyl)methanamine hydrochloride (2.0 g, 8.4 mmol). The reation was stirred at rt overnight, diluted with EtOAc, washed with water, and the organic phase was then dried (Na2SO4) and concentrated in vacuo to afford the crude product, which was purified by silica gel chromatography (EtOAc/heptane gradient) to give the title compound as a white powder (2.21 g, yield: 92percent). LCMS: RT 1.59 mm.; MH+ 350.0; ?H NMR (400 MHz, DMSO-d6) 5: 8.41 (t, J = 5.65 Hz, 1H), 8.29 (s, 1H), 7.89 (s, 1H), 7.28 – 7.44 (m, 2H), 7.16 (d, J = 8.03 Hz, 1H), 4.34 (d, J = 5.52 Hz, 2H), 2.30 (s, 3H), 1.52 (s, 9H).

According to the analysis of related databases, 376646-62-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 6698-13-1, A common heterocyclic compound, 6698-13-1, name is 4-Bromo-1,3-benzodioxole, molecular formula is C7H5BrO2, 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.

Tert-butyl piperazine-l-carboxylate (1.11 g, 5.97 mmol) was added to a solution of 4- bromobenzo[d][l,3]dioxole (1 g, 4.97 mmol ) in Toluene (15.0 ml). The resulting suspension was degassed using a stream of argon. Cesium carbonate (2.27 g, 558 mu, 6.96 mmol), racemic- 2,2 -bis(diphenylphosphino)-l, -binaphtyl (232 mg, 373 muiotaetaomicron, Eq: 0.075) and Palladium (II) Acetate (55.8 mg, 249 muiotaetaomicron,) were added to this mixture. The reaction was then heated at 100 C over night. The reaction was cooled to rt, 40ml of water was added and the mixture was extracted with Ethyl Acetate ( 2x 80ml). The organic layers were dried over MgS04 and concentrated under vacuum. The crude material was purified by flash chromatography (silica gel, 50g, 0% to 50% EtOAc in heptane). to yield tert-butyl 4-(benzo[d][l,3]dioxol-4-yl)piperazine-l- carboxylate as a white solid ( 1.15 g, 75%). MS (ISP) m/z = 307.4 [(M+H)+].

The synthetic route of 6698-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; RODRIGUEZ SARMIENTO, Rosa Maria; WICHMANN, Juergen; WO2012/110470; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 69902-83-6, 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. 69902-83-6 name is 1-Bromo-2-methyl-3-(trifluoromethyl)benzene, 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.

i). Preparation of 1-bromo-2-(bromomethyl)-3-(trifluoromethyl)benzene (i-4) To a solution of 1-bromo-2-methyl-3-(trifluoromethyl)benzene (i-4a) (2 g, 8.36 mmol) in CCl4 (20 mL) was added NBS (1.49 g, 8.36 mmol), dibenzoyl peroxide (20 mg, 0.08 mmol). The mixture was stirred under nitrogen at 100 C. for 16 h. The solvent was removed in vacuo, and the residue was partitioned between water (15 mL) and DCM (15 mL). The water layer was extracted with DCM (15 mL*3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EtOAc=50/1) to afford the title compound (1.16 g, purity 80%, yield: 43%). LCMS (ESI) calc’d for C8H5Br2F3 [M+H]+: 317. found: 317.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-methyl-3-(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Barr, Kenneth J.; Bienstock, Corey E.; MacLean, John K.; Zhang, Hongjun; Beresis, Richard T.; Anthony, Neville J.; Lapointe, Blair T.; Sciammetta, Nunzio; US2015/210687; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 202865-77-8, name is 2-Bromo-4-fluoro-6-methylaniline, 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. Recommanded Product: 202865-77-8

Step b2-Bromo-4-fluoro-6-methylbenzonitrileA solution of potassium cyanide (16.25 g, 0.25 mol) in 20 mL of water was added to a suspension of freshly prepared copper(l) chloride (9.5 g, 0.096 mol) in 40 mL of water, copper(l) chloride was observed to dissolve initially and then a minute amount of precipitate was formed. Toluene (30 mL) was added and the mixture was chilled to 0 0C in the fridge. 2-Bromo-4-fluoro-6-methylaniline (15.7 g, 0.077 mol) was added to a mixture of 16.5 mL of 36% aqueous hydrochloric acid and 40 mL of water. The resulting suspension was heated until a solution formed. The solution was chilled to 2 0C with an ice bath and the amine hydrochloride precipitated. A solution of sodium nitrite (5.34 g, 0.078 mol) in 15 mL of water was slowly added keeping the reaction mixture temperature below 5 0C (ice bath). A powder of sodium carbonate decahydrate was added in small portions to adjust the pH of the reaction mixture to about 7.A solution of the diazonium salt was slowly added to the cyanocuprate reagent keeping the reaction temperature below 5 0C. A bright red-orange precipitate formed. The reaction mixture was allowed to warm to 20 0C, kept at this temperature for 14 hours. Then it was slowly heated to 70 0C and kept at this temperature for 1 hour. The precipitate dissolved almost completely. The reaction mixture was allowed to cool to 20 0C and filtered. Organic phase was separated and the aqueous phase was extracted with toluene (3 x 70 mL). The combined organic layers were washed with water (2 x 100 mL), brine (2 x 100 mL), dried with sodium sulfate, filtered and concentrated. The crude nitrile (13.9 g, 84 %) obtained was used without further purification.1H NMR (400 MHz, DMSO-de) delta ppm 7.73 (dd, 3JH-F = 8.2 Hz, 4JH-H = 2.1 Hz, 1H, Ar), 7.44 (dd, 3JH-F = 9.4 Hz, 4JH-H =2.0 Hz, 1H, Ar), 2.52 (s, 3H, CH3). 13C NMR (300 MHz, dbeta-DMSO) delta 163.5 (d, 1Jc-F = 257 Hz), 147.8 (d, 3Jc-F = 11Hz), 126.1 (d, 3Jc-F = 11 Hz), 118.4 (d, 2Jc-F = 27 Hz), 117 (d, 2Jc-F = 23 Hz), 115.8, 112.7 (d, 4Jc-F = 3 Hz).

The synthetic route of 2-Bromo-4-fluoro-6-methylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; PAPEO, Gianluca Mariano Enrico; ANATOLIEVNA BUSEL, Alina; CASALE, Elena; KHVAT, Alexander; KRASAVIN, Mikhail Yurievitch; ORSINI, Paolo; POSTERI, Helena; SCOLARO, Alessandra; WO2011/6803; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1159010-96-4, name is 3-Bromo-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, belongs to bromides-buliding-blocks 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 1159010-96-4, Recommanded Product: 1159010-96-4

3-{1-[6-(3-bromo-7,8-dihydro-5H-1,6-naphthyridin-6-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-7-methoxy-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one 90 mg (0.24 mmol) TBTU were added to 80 mg (0.20 mmol) 6-[4-(7-methoxy-2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-pyrimidine-4-carboxylic acid, 70 mg (0.28 mmol) 3-bromo-5,6,7,8-tetrahydro-1,6-naphthyridine-hydrochloride and 120 muL (0.86 mmol) triethylamine in 0.9 mL DMF and the mixture was stirred overnight at RT. The reaction mixture was combined with 1 mL methanol, 1 mL saturated sodium hydrogen carbonate solution and 8 mL ice water. The precipitate was suction filtered, washed with water and diethyl ether and dried. Yield: 94 mg (75% of th.) ESI-MS: m/z=592/594 (M+H)+

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary