Month: March 2021

103977-79-3, name is 3-Bromo-2,4-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. Formula: C6H4BrF2N

To a mixture of 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (1.831 g, 7.21 mmol), potassium acetate (1.415 g, 14.42 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.785 g, 0.962 mmol) under nitrogen was added a solution of 3-bromo-2,4-difluoroaniline (1.0 g, 4.81 mmol) in 1,4-dioxane (20 mL). The mixture was stirred at 100 C. overnight. After cooling to room temperature, the mixture was diluted with DCM and filtered through Celite. The filtrated was concentrated in vacuo. The residue was purified by Biotage Isolera (740 mg, 60%). LCMS calculated for C12H17BF2NO2 (M+H)+ m/z=256.1; found 256.1.

The synthetic route of 103977-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Vechorkin, Oleg; Pan, Jun; Liu, Kai; Sokolsky, Alexander; Wang, Anlai; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; (167 pag.)US2018/72720; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, molecular formula is C14H8Br2, 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. Application In Synthesis of 1,2-Bis(4-bromophenyl)ethyne

General procedure: Diphenylacetylene (36 mg, 0.20 mmol), NFSI (95 mg, 0.30 mmol,1.5 equiv), bathocuproine (8.7 mg, 24 mumol, 12 mol%), CuBr (2.9 mg, 20 mumol, 10mol%) and CsF (30 mg, 0.20 mmol, 1.0 equiv) were added to a Schlenk tubecontaining a magnetic stirring bar in open air. The tube was evacuated and refilledwith N2 gas following the usual Schlenk technique. Anhydrous 1,2-dichloroethane(2.0 mL, 0.10 M) was added into the tube and the reaction tube was capped with a J.Young O-ring tap. The reaction mixture was stirred and heated at 70 C for 12 h.The mixture was then cooled to room temperature. The crude mixture was filteredthrough a pad of silica gel topped with Na2SO4 in a short column and concentrated invacuo. 2-Fluorobiphenyl (17.2 mg, 0.10 mmol) was added into the crude as aninternal standard and the 19F NMR yield was determined. Purification by flashchromatography on silica gel (hexane/EtOAc = 7:1) followed by concentration invacuo provided 2a in 62% (53.3 mg, 0.124 mmol) yield as white crystals.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2789-89-1, its application will become more common.

Reference:
Article; Yip, Shu Jan; Yoshidomi, Tetsushi; Murakami, Kei; Itami, Kenichiro; Chemistry Letters; vol. 47; 3; (2018); p. 329 – 331;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 40161-54-4, A common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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.

EXAMPLE 3 Ex 3a N-[2′-fluoro-4′-(trifluoromethyl)-4-biphenylyl]methanesulfonamide A solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (0.17 mmol), N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide (0.34 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.01 mmol) in 2M aqueous potassium carbonate solution (1.0 mL) and N,N-dimethylformamide (1.0 mL) was heated at 100 C. for 17 h. The reaction mixture was cooled, poured into water (3.0 mL), and extracted with (3*4.0 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and were concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC provided the title product as a white powder (65%). ESMS [M+H]+: 334.2.

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; SMITHKLINE BEECHAM CORPORATION; CYTOKINETICS; US2007/259951; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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 16518-62-0, Safety of 3-Bromo-N,N-dimethylaniline

To a solution of compoundN,N dimethyl-3-bromo aniline (10.0 g, 50.0 mmol) in AcOH (250 mL) was added 12.16 mL of 37% formaldehyde aqueous solution (4.5 g, 150.0 mmol), and the mixture was stirred at 60 C for 115 mm. After cooling to room temperature, a portion of acetic acid was removed by vacuum. Then, the reaction mixture was neutralized with saturated NaHCO3 aq. and NaOH aq., and extracted with CH2C12. The organic layer waswashed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (silica gel) to give pure 4,4?-methylenebis(3-bromo-N,N- dimethylaniline) (5.24 g, 12.7 mmol, 51% yield).

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, 3-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VISEN MEDICAL, INC.; GROVES, Kevin; BUFF, Ryan; WO2014/144793; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1073-06-9,Some common heterocyclic compound, 1073-06-9, name is 1-Bromo-3-fluorobenzene, molecular formula is C6H4BrF, 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.

500ml three-necked flask, magnesium turnings 5.9g (0.24mol), THF20ml,A solution of 38.5 g (0.22 mol) of 3-fluorobromobenzene in 140 mL of THF was added dropwise to prepare 3-fluorophenyl magnesium bromide.Warmed to 60 C,To maintain a steady reaction dropwise 1,4-cyclohexanedione monoethylene ketal 31.2g (0.2mol)And 120ml of toluene dubbed the solution, after the incubation temperature was stirred 3h,Cool to 0 C. Keep the temperature below 10 C slowly add 2N hydrochloric acid 200ml, the upper organic layer was separated,The aqueous layer was extracted once with 120 ml of toluene, the organic phases were combined, the solvent was evaporated to 100 C, 1 g of p-toluenesulfonic acid was added,Ethylene glycol 5g, reflux water 5h to dry out. The reaction solution was washed with aqueous sodium bicarbonate until neutral,Drying toluene,43.1 g (46.8 g) of cyclohexenyl intermediate was obtained in a yield of 92% and a GC purity of 98.6%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-fluorobenzene, its application will become more common.

Reference:
Patent; (11 pag.)CN107573212; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 203302-95-8, These common heterocyclic compound, 203302-95-8, name is 4-Bromo-3,5-difluoroaniline, 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.

mixture of 4-bromo-3,5-difluroaniline (400 mg, 1.923 mmol) and NCS (257 mg, 1.923 mmol) in DMF (3.8 mL) was stirred at 60C for 90 min. It was diluted with diethyl ether (40 mL), washed with water (20 mL), and brine (20 mL). The organic layer was dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (eluting with EtOAc/hexane = 50%) to give the title compound. MS (ES+) m/z: 242, 244 (M+H).

Statistics shows that 4-Bromo-3,5-difluoroaniline is playing an increasingly important role. we look forward to future research findings about 203302-95-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); A1;,
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. 75024-22-5, name is 1,4-Dibromo-2,3-dimethylbenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,4-Dibromo-2,3-dimethylbenzene

100 g (380 mmol) of 1,4-dibromo-2,3-dimethylbenzene are dissolved in 1500 ml of dry diethyl ether, 420 ml (840 mmol) of a 2 M solution of n-butyllithium in cyclohexane are added dropwise at -70 C., after 1 h 130 ml of trimethyl borate (1140 mmol) are added dropwise, the mixture is allowed to come to RT over the course of 1 h, the solvent is removed, 90 g (76 mmol) of pinacol and 1000 ml of toluene are added, the mixture is heated at the boil for 2 h, the solvent is removed again, and the residue, which is homogeneous according to 1H-NMR, is employed in the subsequent reaction without further purification.

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; US2011/92701; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, 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 454-79-5, name: 2-Bromo-5-(trifluoromethyl)aniline

Example 20-1: General procedure for Stille coupling, exemplified by synthesis of compound 2-Pyridin-2-yl-5-trifluoromethyl-phenylamine (108).; A screw cap tube was charged with 2-tributyltinpyridine (1.4 eq), prepared from 2- bromopyridine and tributyltin hydride according to the procedure described in example 19-1, o-bromoaniline (200 mg, 1 eq), Pd(dba)2 (10-14 mg, 2 mol%), CuI (20 mg, 10 mol%), and PPh3 (40 mg, 15 mol%). The mixture was degassed and back-filled with argon. Dry diethyl ether (5 ml) was added, and the reaction mixture was heated at 120C for 4h in a microwave oven. The reaction mixture was cooled to room temperature, stirred with saturated aqueous KF (3 ml) for 3h, and filtered. The solid was discarded after washing with ethyl acetate (three times). The liquid was poured into H2O and extracted with ethyl acetate. The combined organic layer was washed with H2O and brine, dried over MgSO4, and filtered and the solvent was removed in vacuo. The residue was purified by column chromatography on silica (ethyl acetate/petroleum ether as eluent) to afford the title compound as a white solid (60 mg, 38%). M+ 239.

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; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2007/14922; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

58971-11-2, name is 3-Bromophenethylamine, 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. SDS of cas: 58971-11-2

To a cooled (ice bath) solution of 3-bromophenethylamine (21 g, 105 mmol) and TEA (12.7 g, 125 mmol) in DCM (150 mL) was added dropwise trifluoroaceticanhydride (24 g, 115 mmol). The reaction was stirred at room temperature for18 h then poured into water (200 mL) and extracted with DCM (2 x 200 mL). The combined organic layers were concentrated then diluted with methyl tert-butyl ether (TBME) (250 mL) and H20 (50 mL). The layers were separated and the organic phase was washed with brine (50 mL) then dried over Na2504,filtered and concentrated to give crude N-(3-bromophenethyl)-O-(2,2,2-trifluoro- acetyl) hydroxylamine (33 g, >100%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) O [ppm] 9.49 (br 5, 1H), 7.47- 7.35 (m, 2H), 7.30- 7.17 (m, 2H), 3.42 (d, J=4.0 Hz, 2H), 2.80 (t, J=7.0 Hz, 2H).

The synthetic route of 58971-11-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; ITEOS THERAPEUTICS; NINKOVIC, Sacha; CROSIGNANI, Stefano; SCALES, Stephanie Anne; MCALPINE, Indrawan James; COLLINS, Michael Raymond; MADERNA, Andreas; WYTHES, Martin; (295 pag.)WO2016/147144; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 68322-84-9,Some common heterocyclic compound, 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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.

Cul (150 mg, 0.79 mmol) and N,/V-dimethylethylenediamine (0.17 mL, 1.58 mmol) were added to a mixture of 3-bromo-4-fluorobenzotrifluoride (768 mg, 3.16 mmol), intermediate 21 (250 mg, 0.79 mmol), and Cs2C03 (644 mg, 1.98 mmol) in DMF (3 mL). The r.m. was heated at 170 C for 90 min twice, the r.m. was cooled, EtOAc was added and the mixure was washed with a IM aq. H4OH solution, water and brine. The organic layer was dried (MgS04), filtered and the solvent was evaporated in vacuo. The residue was purified by flash column chromatography (eluent: DCM/MeOH from 100/0 to 97/3). The product fractions were collected and concentrated in vacuo. Then the residue was repurified by RP preparative HPLC [RP Vydac Denali C18 – IotaOmicronmu?iota, 250 g, 5cm); mobile phase: a gradient of (0.25% H4HC03 sol. in water)/CH3CN)]. The product fractions were collected and concentrated in vacuo. Yield: 75 mg of compound 14 (20 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; BISCHOFF, Francois, Paul; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2012/126984; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary