Tag: M.W=200-300

Reference of 13633-25-5, A common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, molecular formula is C10H13Br, 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: General Procedure 3: An oven-dried 12.0 ml_ Schlenk tube containing a stirring bar was charged with the compound of formula (Ilia) (20 mol%, 16.8 mg, 0.06 mmol), L2 (10 mol%, 8.1 mg, 0.03 mmol), alkyl bromide (0.30 mmol, if solid), CF3C02Na (1.0 eq, 40.8 mg, 0.3 mmol). The schlenk tube was transferred to a nitrogen-filled glove-box where the Ni(acac)2 (10 mol%, 7.7 mg, 0.03 mmol), Na2C03 (1.0 eq, 32.0 mg, 0.30 mmol), alkyl bromide of formula R?-Br (0.30 mmol, if liquid) and anhydrous THF (0.075 M, 4ml_) were added. Then, the mixture was stirred for 1 minute and taken out of the glovebox. The Schlenk tube was placed approximately ~3 cm away from two 32 W CFL and it was rigorously stirred for 36- 96 h. After completion of the reaction, the crude material concentrated under reduced pressure. The desired product was directly purified by flash column chromatography in silica gel with pentane/EtOAc.

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; FUNDACIO INSTITUT CATALA D’INVESTIGACIO QUIMICA (ICIQ); INSTITUCIO CATALANA DE RECERCA I ESTUDIS AVANCATS (ICREA); MARTIN ROMO, Ruben; SHEN, Yangyang; GU, Yiting; (56 pag.)WO2019/96832; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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,
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

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

Adding a certain compound to certain chemical reactions, such as: 53965-69-8, name is 4-Bromo-2,3,5,6-tetramethylaniline, 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 53965-69-8, Application In Synthesis of 4-Bromo-2,3,5,6-tetramethylaniline

n the S104, the third intermediate (2.25 g, 5 mmol), 4-bromo-2,3,5,6-tetramethylaniline (1.39 g, 6 mmol) in argon was added to a 250 mL two-necked flask. In a gas atmosphere, 100 mL of acetone with water and oxygen removed in advance was injected, and the reaction was performed at 60 C for 24 hours. The reaction solution was poured into 200 mL of ice water, and extracted with dichloromethane three times. The organic phases were combined, and the mixture was separated into silica gel by column chromatography (dichloromethane: n-hexane, v: v, 1: 1) to obtain 2.41 g of a white powder. The yield is 80%. MS (EI) m / z: [M] +: 604.13. The theoretical relative molecular mass of the first reactant is 604.25.

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; Wuhan Hua Xing Optoelectric Semiconductor Display Co., Ltd.; Luo Jiajia; (18 pag.)CN110511223; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

To a stirred suspension of Intermediate B (523 mg, 2.46 mmol), terf-butyl 4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1 (2H)-carboxylate (Eastwood, P. R. Tetrahedron Lett. 2000, 41, 3705) (950 mg, 3.07 mmol), and 1,1′- bis(diphenylphosphino)-ferrocene]dichloro palladium(ll)-complex with dichloromethane (180 mg, 0.25 mmol) in degassed DME (18 mL) was added aqueous Na2CO3 solution (2 M, 3.7 mL). The reaction was heated (80 0C) for 17 h and then cooled to rt. The mixture was partitioned between ethyl acetate (50 mL) and H2O (50 mL). The layers were separated and the organic layer was washed with brine (25 mL), dried (Na2SO4), and concentrated to dryness. The crude residue was purified by ISCO chromatography using a gradient of 50 to 75% ethyl acetate in hexanes to afford 584 mg (75%) of the desired product as an off-white solid, which contained trace impurities. 1H NMR (300 MHz, DMSO-d6) delta 7.85 (s, 1 H), 7.68 (br s, 2 H), 6.97 (br s, 1 H)1 6.87 (d, 1 H), 6.66 (d, 1H), 4.07-4.00 (m, 2 H), 3.53 (t, 2 H), 2.56-2.50 (m, 2 H), 1.42 (s, 9 H); ES-MS m/z 316.1 [MH-H]+, HPLC RT (min) 2.31.

The chemical industry reduces the impact on the environment during synthesis 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 58971-11-2,Some common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, molecular formula is C8H10BrN, 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 116: 5-(1 -cyclohexyl-5-(methoxymethyl)-1 H-pyrazol-4-yl)-3-(1 ,2,3,4- tetrahydroisoquinolin-6-yl)-1 ,2,4-oxadiazoleStep 1: N-(3-bromophenethyl)-2,2,2-trifluoroacetamide; To a solution of 3-bromophenethylamine (2.46 g; 12.3 mmol) in DCM (15 mL) was added diisopropylamine (3.18 g; 24.6 mmol) and trifluoroacetic anhydride (2.84 g; 13.5 mmol) and the mixture was stirred for 16 hours. The solvent was removed in vacuo and the residue was triturated with DCM (1 mL) and petrol (10 mL) to give the title compound (2.57 g; 70 %) as a pale yellow solid. 1H NMR (CDCI3, 400MHz) delta 7.40 (1 H, d, J = 8.0 Hz), 7.36 (1 H, s), 7.21 (1 H, t, J = 7.8 Hz), 7.12 (1 H, d, J = 7.7 Hz), 6.37 (1 H, br s), 3.65-3.57 (2 H, m), 2.87 (2 H, t, J = 7.1 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromophenethylamine, its application will become more common.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; BAKER-GLENN, Charles; BLACKABY, Wesley; KNIGHT, Chris; WO2010/142628; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary