Category: bromides-buliding-blocks

Application of 1193389-40-0, These common heterocyclic compound, 1193389-40-0, name is 1-(4-Bromophenyl)cyclobutanamine hydrochloride, 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.

The free base of commercially available [1 -(4-bromo-phenyl)-cyclobutyl]-amine hydrochloride [CAS 1 193389-40-0] (8.99 g, 34.24 mmol) was prepared as follows: (8.99 g, 34.24 mmol) of the hydrochloride salt was taken up in DCM and washed sequentially with aqueous sodium bicarbonate and water and the organic portion was dried and concentrated.

The synthetic route of 1193389-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; INCE, Stuart; REHWINKEL, Hartmut; HAEGEBARTH, Andrea; POLITZ, Oliver; NEUHAUS, Roland; BOeMER, Ulf; WO2012/7416; (2012); A1;,
Bromide – Wikipedia,
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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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-2,5-difluorobenzene

To a solution of 2-bromo-l,4-difluoro-benzene (3.01 g, 15.60 mmol, 1.20 Eq) in THF (15 mL) was added isopropyimagnesium chloride complex (2.27 g, 15.60 mmol, 1.20 Eq) at 0C dropwise under N2. The reaction was stirred at 15C for 1 hr to prepare (2, 5-difluorophenyl) magnesium bromide (23 mL). To a solution of tert-butyl (R)-4-((tert-butyldiniethyl.silyl)oxy)-2- oxopyrrolidine-l-carboxylate (4.10 g, 13.00 mmol, 1.00 Eq) in THF (50 mL) was added (2,5- difluorophenyl) magnesium bromide (23 mL) dropwise at ()C over 30 mins. The reaction mixture was stirred at 0C for 1 hr. Methanol (20 mL) was added to the mixture followed by NaBH4 (738 mg, 19.50 mmol, 1.50 Eq) at 0C. The mixture was stirred at 0C for 1 hr then poured into 10% aqueous NH4CI. The mixture was extracted with EtOAc (20 mL*2), the combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The crude product was purified by medium pressure liquid chromatography (MPLC) to give tert-butyl ((2R)-2-((tert- butyldimethylsilyl)oxy)-4-(2,5-difluorophenyl)-4-hydroxybutyl)carbamate (2.22 g, 5.14 mmol, 39.6% yield). 1H-NMR (400 MHz, CDC13) delta ppm 7.17-7.15 (m, 1H), 6.86-6.79 (m, 2H), 5.11-5.06 (m, 1H), 4.70 (br.s, 1H), 4.02-3.98 (m, 1H), 3.69 (br.s, 0.5H), 3.46 (br.s, 0.5H), 3.33-3.14 (m, 2H), 1.80-1.69 (m. 2H), 1.35 (s. 9H), 0.84-0.82 (9H, m), 0.04-0.03 (6H, m).

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; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; BROOIJMANS, Natasja; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil; (206 pag.)WO2017/35354; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 50670-49-0,Some common heterocyclic compound, 50670-49-0, name is 4-Bromo-4′-methyl-1,1′-biphenyl, molecular formula is C13H11Br, 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 1.15; Preparation of (4-Bromo-2-methyI-2H-pyrazol-3-yl)-(4′-methyl-biphenyl-4-yl)-amine (Compound 9).A 20-mL scintillation vial was charged with 4′-bromo-4-methyl-biphenyl (247.1 mg, 1 mmol), 3-amino-4-bromo-2 -methyl pyrazole (176.0 mg, 1 mmol), sodium fert-butoxide (134.5 mg, 1.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (45.8 mg, 0.05 mmol), BINAP (62.3 mg, 0.1 mmol) and toluene (2 mL) under nitrogen atmosphere. The reaction mixture was heated at 800C for 48 hours. It was then allowed to cool to room temperature, taken up in ether/ethyl acetate, filtered and concentrated. The crude material was subjected to column chromatography on silica gel (Biotage, eluent hexanes/ethyl acetate 70/30) to afford Compound 9 as a yellow solid. LCMS m/z (%) = 342 (M+H 79Br, 100), 344 (M+H 81Br, 98).

The synthetic route of 50670-49-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2006/60762; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 25121-87-3, name is 2,5-Dibromothieno[3,2-b]thiophene, A new synthetic method of this compound is introduced below., COA of Formula: C6H2Br2S2

Tetrakis(triphenylphosphine)palladium(0) (0.05 g) was added to a solution 2,5-dibromothieno [3,2-b]thiophene (0.10 g, 0.34 mmol) in dry THF (30 ml), with stirring, under nitrogen. After 20 min, 2-{5-[6-(tert- Butyldimethylsilanyloxy)-hexyl]-thieno[3,2-b]thiophen-2-yl}-4,4,5,5- tetramethyl-[1,3,2]dioxaborolane (0.49 g, 1.02 mmol ) and a solution of potassium carbonate (0.28 g, 2.04 mmol) in water (10 ml) was added. The resultant mixture was heated at reflux for 1.5 h. After cooling, water (100 ml) was added and the precipitate filtered off, washed with water and diethyl ether, to give a yellow solid, which was recrystallised with toluene to give 5 as yellow crystals (0.23 g, 82 %). LC Phases: K – 88C – Sx – 229C – SX1 – 290C – I. ?H NMR (300 MHz, CDC13): 8 (ppm) 7.30 (s, 2H, Ar-H), 7.28 (s, 2H, Ar-H), 6.91 (s, 2H, Ar-H), 3.61 (t, J = 6.4 Hz, 4H, OCH2), 2.88 (t, J = 7.5 Hz, 4H, ArCH2), 1.35-1.80 (m, 16 H, CH2), 0.90 (s, 18 H, CH3), 0.05 (s, 12 H, CH3); ??C NMR (75 MHz, CDC13): 8 (ppm) 148.9 (quat.), 139.4 (quat.), 138.4 (quat.), 137.8 (quat.), 137.7 (quat.), 137.3 (quat.), 116.4 (CH), 116.1 (CH), 115.4 (CH), 63.2 (OCH2), 32.8 (CH2), 31.6 (CH2), 31.2 (CH2), 28.9 (CH2), 26.0 (CH3) 25.6 (CH2), 18.4 (quat.), -5.2 (CH3)

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; MERCK PATENT GMBH; WO2005/121150; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 314084-61-2 as follows. Recommanded Product: 2-Bromo-1,3-diethyl-5-methylbenzene

Step 2: Set up a 1000mL four-neck bottle, thermometer,Three-way nitrogen ball device, the system uses an oil pump to pump vacuum and use nitrogenAfter gas replacement for three times, under nitrogen protection,Add 100 mL of tetrahydrofuran to the system.2,6-Diethyl-4methylbromobenzene 20g (molecular weight 227.1, 0.088mol), cooled to -60 C, control the temperature of the reaction solution between -50 C and -60 C, slowly add 528 mL 1 mol / L positive Butyl lithium in n-hexane solution (0.528 mol),After the addition was completed, the temperature was kept at -50 C to -60 C for 1 h.16.49 g of 2-bromoethanol (molecular weight 124.96, 0.132 mol) was slowly added dropwise at -50 C to -60 C, and the reaction was kept after the addition.0.5h. The reaction solution was quenched with 50 mL of 1 mol/L diluted hydrochloric acid and extracted twice with 50 mL of ethyl acetate.To dryness, 16.3 g of a colorless oil was obtained. After 10 min, the oil was turned to white solid.

According to the analysis of related databases, 314084-61-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Zhongqi Technology Co., Ltd.; Bu Long; Zhang Pu; Qian Ziwei; Gao Miao; Wang Fengyun; Hou Yuanchang; (10 pag.)CN109651068; (2019); A;,
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. 583-70-0, name is 2,4-Dimethylbromobenzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H9Br

(e) (2,4-dimethyiphenyl)(phenyl)methanamine hydrochloride: To a suspension of Mg (1.32g, 55 nunol) in TI-iF (60 mnL) was added a catalytic aniount of 12 and ibrorno-2,4diniethylbenzene(0.5 g). The reaction was initiated by heating and then additional i-bromo-2,4-dimethylbenzene (8.75 g) was added dropwise. The mixture was stirred at it for 4 h under nitrogen. Benzonitrlie (5.15 g, 50 mmol) was added dropwise into the solution . After the addition, the reaction mixture was stirred at it for 16 Ii. Then the reaction was quenched by the addition 20 mL of MeOH,followed by NaBI-i, (1.9 g, 50 mniol) in portions. After stirring at rt for 5 h, the reaction was quenched by the addition of 20 nL water. Solvent was removed under reduced pressure. The residue was extracted with EtOAc (3 x 100 mE). IN aq. HCI was added to the combined organic layers during which a white solid precipitated. The white solid was collected by filtration (8.8 g, 84%). LCMS-Pi: 195 FM-NT-I2]4 IT-, = 1.232 mm. ?El NMR (500 MHz, DMSO-d6) 6 ppm9.15 (s, 2H), 7.55 (d,J 8.0 Hz, iT-i), 7.45 7.32 (in, 5Ff), 7.12 (d,.1 8.0 Hz, IT-i), 7.04 (s, iFi),5.64 5.62 (in, 1H), 2.27 (s, 3H), 2.22(s, 3H).

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19626; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, 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: (Bromomethyl)cyclopentane

Example 8A 2-(Trimethylsilyl)ethyl (1RS,2RS,5SR)-2-[4-(cyclopentylmethoxy)benzoyl]-5-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl]cyclopentanecarboxylate (racemate) To a solution of 80 mg (0.16 mmol) of the compound from Example 4A in 1.8 ml of acetonitrile were added 45 mg (0.32 mmol) of potassium carbonate and 32 mg (0.19 mmol) of (bromomethyl)cyclopentane, and the mixture was stirred under reflux overnight. Thereafter, a further 32 mg (0.19 mmol) of (bromomethyl)cyclopentane were added, and the mixture was stirred under reflux once again for 4 h. After cooling to RT, the mixture was diluted with water and extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated. The residue was purified by means of preparative HPLC (Method 7). 33 mg (36% of theory, 100% purity) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.61 min, m/z=576 [M+H]+.

The synthetic route of (Bromomethyl)cyclopentane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Pharma Aktiengesellschaft; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMANN, Andreas; BROHM, Dirk; JOeRISSEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (91 pag.)US2017/22171; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 57190-17-7, name is 2-Bromo-1,3-diisopropylbenzene, 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 57190-17-7, SDS of cas: 57190-17-7

[0558] Step 4: 5-Chloro-2-(2,6-diisopropylbenzoyl)-6-(2-fluorophenyl)nicotinic acid with 5-chloro-3-(2,6-diisopropylbenzoyl)-6-(2-fluorophenyl)picolinic acid. 2-Bromo-1,3- diisopropylbenzene (1.00 g, 4.15 mmol, Combi-Blocks, San Diego, CA) was added to a mixture of magnesium turnings (106 mg, 4.35 mmol) and iodine (3 mg, 0.012 mmol) in tetrahydrofuran (6 mL) under an argon atmosphere. The reaction mixture was heated to 65 C for 2.5 h. The reaction mixture was cooled to room temperature and 5 mL of the Grignard solution were added dropwise to a stirred solution of 3-chloro-2-(2-fluorophenyl)furo[3,4- b]pyridine-5,7-dione (321 mg, 1.156 mmol) in tetrahydrofuran (5 mL) at -78 C under an argon atmosphere. The reaction mixture was stirred at -78 C for 1 h and then allowed to warm to room temperature and stir for another 1 h. The reaction mixture was quenched with saturated aqueous ammonium chloride (50 mL) and extracted with EtOAc (75 mL). The organic layer was separated, washed with brine (60 mL), dried over MgSO4, filtered, and concentrated in vacuo to give approximately a 1:4 mixture of 5-chloro-2-(2,6-diisopropylbenzoyl)-6-(2- fluorophenyl)nicotinic acid with 5-chloro-3-(2,6-diisopropylbenzoyl)-6-(2- fluorophenyl)picolinic acid. m/z (ESI, +ve ion ion): 440.1 (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; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 608-30-0,Some common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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 Synthesis of 2,6-dibromobenzenesulfonyl chloride A solution of 2,6-dibromoaniline (10 g, 39.8 mmol) in trifluoroacetic acid (60 mL) and conc. HCl (12 mL) was cooled to 0 C. in an ice bath and treated dropwise with a solution of sodium nitrate (3.4 g, 39.8 mmol) in water (3 mL) over a period of 60 min. To the resulting mixture was added a suspension of copper(I) chloride (2.6 g) and copper(II) chloride (2.6 g) in sulfurous acid (70 mL) and acetic acid (70 mL) over a period of 90 min. After the addition was complete the resulting mixture was stirred at ambient temperature for 45 min. The resulting white precipitate was collected by filtration and dried under the reduced pressure to afford 2,6-dibromobenzenesulfonyl chloride as the white powder (5.2 g, 39%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,6-Dibromoaniline, its application will become more common.

Reference:
Patent; Wexler, Ruth R.; Jacobson, Irina C.; US6399644; (2002); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 103-64-0, name is (2-Bromovinyl)benzene, A new synthetic method of this compound is introduced below., name: (2-Bromovinyl)benzene

At room temperature under a nitrogen atmosphere, to an appropriate amount of organic solvent (volume ratio 2: a mixture of methyl tetrahydrofuran and 2-propanol 1) were added successively compound 100mmol formula (I), 170mmol compound of formula (II), (III) compounds, 20mmol composite catalyst 300mmol formula (a 6mmolPd2 (dba) 3 with 14mmol trimethylphosphine (hexafluoroacetylacetonato mixture) of copper), 10mmol 300mmol gallium trichloride and an organic base2,4-lutidine, then warmed to 85 sufficiently stirred and incubated for 4 hours;After completion of the reaction, the reaction system was filtered, and the filtrate was cooled to room temperature, and then adjusting pH to neutral, and deionized water was added and washed thoroughly shaken, and extracted 3 times with chloroform, the organic phases combined, dried over anhydrous magnesium sulfate, distillation under reduced pressure, the resulting residue was purified by column chromatography on silica gel, ethyl acetate, acetone and the like in a volume ratio of washing liquid, to afford the compound of formula (IV of), in a yield of 97.6%

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; Li, Naiwen; (12 pag.)CN105218553; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary