Tag: M.W=200-300

Electric Literature of 6698-13-1,Some common heterocyclic compound, 6698-13-1, name is 4-Bromo-1,3-benzodioxole, molecular formula is C7H5BrO2, 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.

[0154] A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (1.4 g, 9.7 mmol), 4-bromo- benzo[l,3]dioxole (2.0 g, 10 mmol), Pd2(dba)3 (0.80 g, 0.87 mmol), Xantphos (1.0 g, 1.7 mmol) and cesium carbonate (6.3 g, 19 mmol) was suspended in dioxane (40 mL) and heated at reflux under the argon atmosphere for 5 h. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and the filtrate concentrated in vacuo. The residue was purified by flash chromatography on silica gel (hexanes to 50% EtOAc/hexanes) to afford the title compound (1.0 g, 39%) as a white solid. 1H NMR (500 MHz, DMSO-d6): delta 2.13 (s, 3H), 5.99 (s, 2H), 6.80-6.90 (m, 3H), 8.01 (s, IH), 8.92 (s, IH). MS (ES+): m/z 264 (M+H)+.

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

Reference:
Patent; TARGEGEN, INC.; WO2007/53452; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 627526-90-3, 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. 627526-90-3, name is 1-Bromo-3-(difluoromethyl)-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

steps 3-5; – /?-Methoxybenzyl alcohol (36.8 g, 266.7 mmol) was added slowly to a mixture of potassium t-butoxide (28.7 g, 255.5 mol) and THF (250 mL). After stirring for about 15 min, 30 (50.O g, 222.2 mmol) was added and the reaction mixture heated to about 65 C. After stirring at 65 C for 2 h, the reaction is analyzed by HPLC. After cooling to RT, a mixture of saturated NaHCO3 solution (150 mL) and water (150 mL) was added. Toluene (300 mL) was added, the organic phase separated and washed with a mixture of saturated NaHCO3 solution (75 mL) and water (75 mL). Polish filtration and concentration in vacuo provided 83.9 g of crude 32 as an oil which is used without further purification.To a solution of crude 32 in NMP (180 ml) was added potassium ferrocyanide(31.1 g, 84.44 mmol) and Na2CO3 (23.55 g, 222.2 mmol). The resulting slurry was degassed thoroughly via repeated evacuation and purging with nitrogen. The slurry was heated to about 100 C and a solution of Pd(OAc)2 (150 mg, 0.67 mmol) and DPPF (505 mg, 0.91 mmol) in degassed NMP (20 mL) added. The mixture was heated to ca. 130 C for about 3 h. HPLC analysis indicated ca. 5% starting material remained. Additional Pd(OAc)2 (50 mg, 0.22 mmol) is added and heating at 130 C was continued for 1.5 h when HPLC analysis showed complete conversion.After cooling toluene (400 mL) and saturated sodium sulfite solution (10 mL) are added and mixture heated at ca. 40 C for about 1 h. Solka-floc (10 g) was added and the mixture was filtered through a bed of Solka-floc and the cake was washed with toluene {ca. 100 mL total). The filtrate was washed successively with dilute sodium sulfite solution (1 x 400 mL) and water (2 x 200 mL). The combined aqueous phases are extracted with toluene (1 x 100 mL) and the toluene back extracted with water (2 x 50 mL). The combined organic phases are polish filtered, and concentrated in vacuo to obtain 70.4 g of 34 as a dark-colored oil (70.4 g) which was used in the next step without further purification.To the solution of crude 36 in toluene (190 mL) and anisole (65 mL) is added TFA (25.3 g, 222.2 mmol). The reaction was heated to ca. 65 C and stirred for about 2 h until the reaction was complete by HPLC. The mixture was distilled in vacuo to remove most of the TFA. After cooling, the mixture is extracted twice with ca. 10% Na2CO3 solution (300 mL then 150 mL). The combined aqueous phases were acidified to a pH of 5.5 with con HCl and extracted with EtOAc (2 x 200 mL). The combined organic phases were washed with water (1 x 150 ml), polish filtered and the solvent replaced with toluene by vacuum distillation. The solution was concentrated to ca. 200 mL, then heptane (200 mL) was slowly added and the mixture heated to 80 C. The mixture was cooled to RT, aged overnight, filtered, and washed with 50% heptane in toluene {ca. 30 mL). The isolated product was dried in vacuo at ca. 60 C to afford 29.0 g (77.2% yield over 3 steps)of 36.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-(difluoromethyl)-5-fluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/145563; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103275-21-4, 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. 103275-21-4, name is 3-Bromo-4-(tert-butyl)aniline, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 3-bromo-4- tert-butyl-phenylamine (5.00 g, 21.92 mmol) in 80 mL of DCM and 25 mL of methanol was added calcium carbonate (4.39 g, 43.83 mmol), followed by iodinating reagent (8.55 g, 21.92 mmol). The reaction was stirred for 3 h at room temperature, quenched with water 100 mL, and the product extracted into ethyl acetate (100 mL). The organic layer was washed with brine (75 mL), dried over magnesium sulfate and concentrated. Silica gel chromatography eluting with 25% ethyl acetate/hexane gave the product as an oil (4.50 g, 12.7 mmol, 58%) : 1H NMR (400 MHz, CDC13) 6 7. 61 (s, 1 H), 6.99 (t, J = 0.9 Hz, 1H), 3 : 96 (s, 2H), 1.44 (s, 9H); MS (ESI) 356.3.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-(tert-butyl)aniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/70407; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1150102-47-8, 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. 1150102-47-8, name is 6-Bromo-N1-methylbenzene-1,2-diamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromo-N2-methyl-benzene-1,2-diamine (20.0 g, 99.4 mmol) in ACN (300 mL) was added CDI (32.2 g, 198 mmol). The reaction mixture was stirred at 85 C. for 12 hours under N2 atmosphere. On completion, the reaction mixture was concentrated in vacuo. The reaction mixture was diluted with water (200 mL), where a solid precipitate was formed, which was filtered off. The solid was washed with water (1 L) and dried in vacuo to give the title compound (20.0 g, 88% yield) as white solid. 1H NMR (400 MHz, DMSO-d6) delta 11.17 (s, 1H), 7.14 (dd, J=1.2, 8.0 Hz, 1H), 7.00-6.95 (m, 1H), 6.93-6.87 (m, 1H), 3.55 (s, 3H).

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, 6-Bromo-N1-methylbenzene-1,2-diamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 3722-78-9, The chemical industry reduces the impact on the environment during synthesis 3722-78-9, name is 8-Bromochroman, I believe this compound will play a more active role in future production and life.

Example 10 8-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)chromane 8-Bromochromane (described in Gerard H. Thomas et al. Tetrahedron. Lett. 1998, 39, 2219-2222, 426 mg, 2 mmol), 4,4,4′,4I,5,5,5′,51-octamethyl-2,2′-bi-l,3,2-dioxaborolane (609 mg, 2.4 mmol), [l,r-bis(diphenylphosphino)ferrocene]palladium(II) chloride dichloromethane adduct (50 mg, 0.06 mmol), potassium acetate (590 mg, 6 mmol) and 1,2- dimethoxyethan (3 mL) was irradiated in a microwave at 150 0C for 15 min. When cooled to ambient temperature the mixture was diluted with water (5 mL) and extracted with diethyl ether (3 x 20 mL). The crude product was purified by flash chromatography, using dichloromethane/methanol (95:5) as the eluent, to give 290 mg (56% yield) of the title compound. 1H-NMR (400 MHz5 OMSO-d6): delta 7.32 (dd, J = 7.3, 1.5 Hz, IH), 7.12 (dd, J = 7.4, 1.6 Hz, IH), 6.76 (t, J = 7.4 Hz5 IH)54.12 (t, J = 5.0 Hz52H)5 2.71 (t, J = 6.5 Hz52H), 1.92-1.84 (m, 2H), 1.25 (s, 12H).

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, 8-Bromochroman, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2007/73284; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

875664-41-8, name is 3-Bromo-4,5-difluoroaniline, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 3-Bromo-4,5-difluoroaniline

N-Boc-(35)-l-pyrrolidine-3-carboxylic acid [CAS 140148-70-5] (1 g, 4.65 mmol), 3-bromo-4,5-difluoroaniline (0.96 g, 4.65 mmol) and HATU (2.12 g, 5.58 mmol) were added to CH2CI2 (10 mL). N,N-diisopropylethylamine (2.4 mL, 13.9 mmol) was added and the resultant mixture stirred at room temperature for 4 hours. The mixture was partitioned with HCl (1M, aq., 20 mL). The organic layer was separated and the solvent removed under reduced pressure. The crude was purified via silica gel column chromatography using a heptane to ethyl acetate gradient to afford an oil. Subsequent Boc deprotection HCl (6 M in isopropanol, 15h at room temperature) afforded (5)-N-(3-bromo- 4,5-difluorophenyl)pyrrolidine-3-carboxamide hydrochloride that was used as such in the next step without further purification.

The synthetic route of 875664-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; WO2015/59212; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 21865-50-9, 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. 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-bromo-2,3,4,9-tetrahydro-lH-carbazole (66 mg, 0.27 mmol) inDMF (3 ml) was added NaH (60% in mineral oil, 16 mg, 0.41 mmol) and tetrabutylammonium iodide (151 mg, 0.41 mmol). The resulting mixture was stirred at room temperature for 10 min and followed by addition of l-(3-chloropropoxy)-3,5- difluorobenzene (55 mg, 0.27 mmol). The reaction mixture was stirred at room temperature overnight, poured into H2O (30 ml), and extracted with EtOAc (3 x 30 ml). The organic layers were combined, dried over MgSO4, filtered and cone, in vacuo. The crude product was purified by silica gel flash chromatography (EtOAc/hexane, 0-20%) to give the title compound (colorless oil, 53 mg). The yield: 46.7%.

The chemical industry reduces the impact on the environment during synthesis 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ITHERX PHARMACEUTICALS, INC.; WO2009/103022; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 128259-68-7, These common heterocyclic compound, 128259-68-7, name is 1,3-Dibromo-2,5-difluorobenzene, 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.

3-fluorophenol (0.099 mL, 1.1 mmol) and KOH (62 mg, 1.1 mmol) were stirred at 50 °C for 30 min before the addition of l,3-dibromo-2,5-difluorobenzene (300 mg, 1.1 mmol) and Cu powder (70 mg, 1.1 mmol). The reaction mixture was heated to 100 °C overnight. The crude material was purified by FC on silica gel (eluent: Cy), giving l-bromo-2,5-difluoro-3-(3-fluorophenoxy)benzene (P5, 61 mg, y= 18percent) as oil. Eta NMR (METHANOL-rf4): delta ppm 7.49-7.38 (m, 1H), 7.33 (ddd, 1H), 7.02- 6.93 (m, 2H), 6.90-6.82 (m, 2H )

Statistics shows that 1,3-Dibromo-2,5-difluorobenzene is playing an increasingly important role. we look forward to future research findings about 128259-68-7.

Reference:
Patent; SHIRE INTERNATIONAL GMBH; CREMONESI, Susanna; MICHELI, Fabrizio; SEMERARO, Teresa; TARSI, Luca; LUKER, Tim; LESLIE, Colin; (121 pag.)WO2016/42453; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-54-7, 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. 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

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 synthetic route of 1,3-Dibromo-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

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; (335 pag.)WO2017/35417; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 28148-04-1, name is 1,3-Dibromo-2-methylpropane, 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 28148-04-1, Recommanded Product: 1,3-Dibromo-2-methylpropane

The beta- lactam carbonyl compound of the formula shown CH3CH2COCH2CONHC6H51.0mmol added 50 ml round-bottomed flask, followed by adding further Cs2CO32.2mmol, eighteen crown six 0.05mmol, acetic 1.2mmol, 1,3- dibromo – 2-methyl propane 1.15mmol and 35mL of deionized water and mix well. The reaction was continued stirring at 40 deg C 5.0 hours, the reaction was stopped by filtration, dried and purified by recrystallization to give 6-anilino after -5- propionyl-3-methyl-3,4-dihydropyran, products yield 87%.

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, 1,3-Dibromo-2-methylpropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Huaihua University; Xiang, Dexuan; Liang, Chunhua; Liu, Yilin; Xiang, Bailin; Zhang, Li; (9 pag.)CN105541770; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary