Month: March 2021

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

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

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

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

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. 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 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

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 74586-53-1, These common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-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.

General procedure: Conventional method: CDI (1.74 g, 0.01 mol) was added to dimethylacetamide solvent (1.0 mL) and were heated to 120-125C for 0.5 h. Cooled the solution to 60-65C and aniline (1.0 g, 0.01 mol) was added. After 1.5 h, HPLC analysis of the crude product showed that the reaction had proceeded to 100% conversion.The reaction solution was cooled to 20-25C and quenched with water (15 mL). The reaction mixture was extracted with isopropyl acetate (2 10 mL). The combined organic layer was washed with 1% aqueous HCl solution (2 10 mL),dried over anhydrous Na2SO4 and filtered. The filtrate was evaporated under vacuum to give 1.3 g (90%) of N-phenylacetamide (Table 2, entry 1).

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chikkulapalli, Anil; Aavula, Sanjeev Kumar; Mona Np, Rifahath; Karthikeyan, Karthikeyan; Kumar C.H., Vinodh; Sulur G., Manjunatha; Sumathi, Shanmugam; Tetrahedron Letters; vol. 56; 24; (2015); p. 3799 – 3803;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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 937046-98-5, Recommanded Product: 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

Intermediate M4 7-Bromo-5-chloropyrrolo[ 1 ,2-f] [ 1 ,2,4]triazin-4-amine To a solution of 7-bromopyrrolo[2, l-fJ[l,2,4]triazin-4-amine (0.48 g, 2.253 mmol) in DMF (11.27 ml) was added NCS (0.361 g, 2.70 mmol) and the reaction mixture was stirred at room temperature for 2 days and was monitored by LCMS. The reaction mixture was partitioned between 1.5M K2HPO4 and EtOAc. The organic phase was washed with 10% LiCl, brine, dried by Na2S04, filtered, and concentrated to afford a white solid as the crude product. The crude product was then purified by ISCO column (24g, 30-50-75% of EtOAc in hexane). The desired product was obtained as a white solid (0.48g) in 86% yield. Mass spectrum m/z 246.8, 248.8, 250.8 (M+H)+. XH NMR (400MHz, DMSO-d6) delta 8.17 (d, J=8.4 Hz, 1H), 7.93 (s, 1H), 7.21 – 7.00 (m, 1H), 6.98 (s, 1H).

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, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; RUAN, Zheming; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; DHAR, T.G. Murali; GONG, Hua; MARCOUX, David; POSS, Michael A.; QIN, Lan-ying; SHI, Qing; TINO, Joseph A.; (126 pag.)WO2016/64958; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary