Month: September 2021

Electric Literature of 59907-13-0, These common heterocyclic compound, 59907-13-0, name is 2-Bromo-1-fluoro-3-methylbenzene, 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.

A 10 mL round-bottomed flask was charged with 2-bromo-l-fluoro-3- methylbenzene (0.13 mL, 0.70 mmol, Sigma-Aldrich, St. Louis, MO) and tetrahydrofuran (2.0 mL). The solution was cooled to -78 C, n-butyllithium (0.28 mL of a 2.5 M solution with hexane, 0.70 mmol, Sigma-Aldrich, St. Louis, MO) was added, and then the reaction mixture was stirred for 30 min. After that time, a solution of N-(l-benzofuran-2-ylmethylidene)-3,4-dihydro-2H-l,5- benzodioxepine-7-sulfonamide (intermediate A) (0.10 g, 0.28 mmol) and tetrahydrofuran (3.0 mL) was added. After stirring for 1 h, water (0.10 mL) was added, and the reaction mixture was warmed to room temperature andconcentrated. The residue was subjected to reversed-phase preparative HPLC (Phenomenex Gemini CI 8 column (Phenomenex, Inc., Torrance, CA)(150 x 30 mm, 5 muiotaeta) eluting with 0.10% trifluroacetic acid in acetonitrile-water, gradient of 10% to 90% over 10 min) to give N-(l-benzofuran-2-yl(2-fluoro-6- methylphenyl)methyl)-3,4-dihydro-2H-l,5-benzodioxepine-7-sulfonamide (0.013 g) as a yellow film (racemic mixture).1H NMR (300 MHz, methanol-d4) delta 7.48 (m, 1 H), 7.36 – 7.30 (m, 2 H), 7.25 – 7.14 (m, 5 H), 6.97 (d, J= 6.0 Hz 1 H), 6.86 (d, J= 9.0 Hz, 1 H), 6.80 (m, 1 H), 6.51 (s, 1 H), 6.11 (s, 1 H), 4.20 – 4.15 (m, 2 H), 4.13 – 4.08 (m, 2 H), 2.41 (s, 3 H), 2.20 – 2.12 (m, 2 H). m/z (ESI, +ve ion) 490.0 (M+Na)+. GK-GKRP EC50 (LCMS/MS) = 0.79 muMu. GK-GKRP IC50 (Binding) = 1.0 muMu.

Statistics shows that 2-Bromo-1-fluoro-3-methylbenzene is playing an increasingly important role. we look forward to future research findings about 59907-13-0.

Reference:
Patent; AMGEN INC.; BARTBERGER, Michael, D.; CROGHAN, Michael, D.; FOTSCH, Christopher, H.; NORMAN, Mark, H.; PENNINGTON, Lewis, D.; REICHELT, Andreas; ST. JEAN, David, J., Jr.; TEGLEY, Christopher, M.; WO2012/138776; (2012); 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. 392-83-6, name is 2-Bromobenzotrifluoride, A new synthetic method of this compound is introduced below., Formula: C7H4BrF3

General procedure: A DMF solution (8mL) of the o-substituted aryl iodide (0.36mmol), the o-bromobenzyl alcohol (0.36mmol) and norbornene (34mg, 0.36mmol) was added under nitrogen to a Schlenck-type flask, containing Pd(OAc)2 (4mg, 0.018mmol), the phosphine (0.036mmol), when required, and K2CO3 (124mg, 0.90mmol) or CsOPiv (211mg, 0.90). The reaction mixture was stirred at 105C for 24h. After cooling to room temperature the organic layer was diluted with EtOAc (20mL), washed twice with water (20mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the resulting residue was purified by flash chromatography on silica gel using mixtures of hexane-EtOAc as eluent.

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:
Article; Della Ca, Nicola; Fontana, Marco; Xu, Di; Cremaschi, Mirko; Lucentini, Riccardo; Zhou, Zhi-Ming; Catellani, Marta; Motti, Elena; Tetrahedron; vol. 71; 37; (2015); p. 6389 – 6401;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 129316-09-2, 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. 129316-09-2, name is 1,3-Dibromo-5-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1 : Benzyl(3-bromo-5-tert-butylphenyl)sulfane (P21a)1,3-Dibromo-5-te?-butylbenzene (2.89 g, 10 mmol) in dioxane (160 mL) was stirred under Ar. Then DIPEA (3.09 mL, 16 mmol), Xantphos (0.28 g, 0.48 mmol) and Pd2(dba)3 (0.24 g, 0.24 mmol) were added and the reaction was heated to 100C. Phenyl-methanethiol (0.94 mL, 8 mmol) was slowly added and the reaction was stirred for 6 h, quenched by the addition of H20 (15 mL) and extracted with EA (3 x). The combined organic layers were washed with water, dried over Na2S04, filtered, evaporated and purified by CC to afford compound P21a (1.7 g, 72%).

The synthetic route of 1,3-Dibromo-5-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHENEX PHARMACEUTICALS AG; STEENECK, Christoph; KINZEL, Olaf; GEGE, Christian; KLEYMANN, Gerald; HOFFMANN, Thomas; WO2012/139775; (2012); 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. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H11Br2N

To a solution of tert-butyl 4-oxo-3- (2-oxo-2-((2,2,2-trifluoroethyl)amino)ethyl)- 1 -phenyl1,3,8-triazaspiro[4.5]decane-8-carboxylate (100 mg, 213 imol, example 17, intermediate b) inACN (1 mL) were added 2-bromo-N,N-dimethylethanamine hydrobromide (59.4 mg, 255 imol; CAS RN 2862-39-7) and cesium carbonate (208 mg, 638 imol) and the suspension was heated at 90C in a sealed tube for 16 hours. After cooling down, the reaction mixture was filtered over a microfilter. The filtrate was treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 4 g column using an MPLC (ISCO) system eluting with agradient of DCM : MeOH (100 : 0 to 90: 10) to get the title compound as a light brown gum (0.024 g; 20.8%). MS (ESI): mlz = 542.3 [M+H].

The synthetic route of 2862-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BUETTELMANN, Bernd; KOCER, Buelent; KUHN, Bernd; PRUNOTTO, Marco; RICHTER, Hans; RITTER, Martin; RUDOLPH, Markus; SATZ, Alexander Lee; (204 pag.)WO2017/5583; (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. 38573-88-5, name is 1-Bromo-2,3-difluorobenzene, A new synthetic method of this compound is introduced below., 38573-88-5

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole 3b (1.22 g, 5 mmol) was dissolved in 20 mL of tetrahydrofuran under stirring under an argon atmosphere, and 1-bromo-2,3-difluoro-benzene (0.97 g, 5 mmol), tetrakis (triphenylphosphine) palladium (0.17 g, 0.15 mmol) and 7 mL of sodium hydroxide solution (2M) were then added to the solution. Upon completion of the addition, the reaction system was stirred at 75°C in an oil bath overnight. The reaction was completed until TLC showed the disappearance of starting materials. The reaction mixture was naturally cooled down to room temperature and extracted with ethyl acetate (20 mL*3). The combined organic extracts were washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to give the title compound 4-(2,3-difluoro-phenyl)-1H-indole 3c (800 mg, yield 70percent) as a white solid. MS m/z (ESI): 228.4[M-1]

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; Jiangsu Hengrui Medicine Co., Ltd.; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2179998; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-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. HPLC of Formula: C6H3BrF2

2,4-difluorobromobenzene (3 g, 15.5 mmol) and 260 mg of iron filings were placed in a two-neck flask, and 15 ml of dichloromethane was then added thereto. The two-neck flask was cooled in an ice bath, and a solution including bromine (1 ml, 18.7 mmol) and 15 ml of dichloromethane was added dropwise to the two-neck flask using an isobaric funnel. Next, the contents in the two-neck flask were heated under reflux for 3 hours. During heating, brown gas was produced. Then, the temperature was reduced to 20 C., and 50 ml of a sodium metabisulfite (Na2S2O5) aqueous solution (10%) was mixed with the contents in the two-neck flask by stirring for 1 hour for terminating the reaction therein. Thereafter, the contents in the two-neck flask were washed several times with deionized water to collect an organic layer, the organic layer was dehydrated using sodium sulfate (Na2SO4), and the solvent in the organic layer was removed, followed by column chromatography (SiO2, n-hexane), thereby obtaining white crystals (3.5 g, 83% yield). (0067) The spectrum analysis for the white crystals is: 1H NMR (400 MHz, CDCl3): delta 7.74 (t, J=7.6 Hz, 1H), 6.96 (t, J=8.0 Hz, 1H); 19F NMR (376 MHz, CDCl3, 298 K): delta -103.8 (dd, J=7.5 Hz, J=7.5 Hz). The white crystals were confirmed to be Compound L3-1 having a chemical structure represented by

The synthetic route of 1-Bromo-2,4-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NATIONAL TSING HUA UNIVERSITY; Chi, Yun; Tong, Bi-Hai; Duan, Tai-Nan; Ku, Hsiao-Yun; Chen, I-Jen; US9219237; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 38573-88-5, These common heterocyclic compound, 38573-88-5, name is 1-Bromo-2,3-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.

Add slowly a solution of 1-methyl-piperidin-4-ol (2.98 g) in DMF (20 mL) into a suspension of sodium hydride (95percent) (0.72 g) in DMF (25 mL) at room temperature. Heat the mixture in an oil bath at 65°C. After 30 MIN., add 1-bromo-2-, 3-DIFLUORO-BENZENE (5.0 g) and stir at 65°C. After 2 hr. , partition the reaction mixture between water and ether, dry over ANHYDROUS sodium sulfate, and evaporate to give a yellow oil. Separate on a silica gel column (110 g, solvent: ether, ETHER-2M NH3 in methanol 19: 1,9 : 1) to obtain 4- (2-bromo-6-fluoro-phenoxy)-1-methyl-piperidine (4.06 g, 54percent yield) and the title compound (1.60 g, 21percent yield). Mass spectrum (electric spray) M/Z = 288 (M+L), 290 (M+2+1) ;1H NMR (CDC13) : 7.12 (m, 1H), 6.92 (m, 2H), 4.30 (m, 1H), 2.69 (m, 2H), 2.30 (s, 3H), 2.28 (m, 2H), 1.97 (m, 2H), 1. 89 (m, 2H).

The synthetic route of 38573-88-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/94380; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, 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. category: bromides-buliding-blocks

PREPARATION EXAMPLE 4 (2S)-3-{4-[2-(5-methyl-2-phenyl-1, 3-oxazol-4-yl)-ethoxy]-phenyl}-2-piperazin-1-yl-propionic acid methyl ester (Intermediate 4) Diethanolamine (100 g) and 40% HBr aqueous solution (1000 mL) were mixed and vigorously refluxed for 10 h, while water was removed continuously under reduced pressure during the reaction. The resulting solution was concentrated to give 297 g of a brown liquid. The above brown liquid (47.4 g), Intermediate 3A (4.5 g, 11.8 mmol ) and 150 mL of anhydrous ethanol were mixed with refluxing overnight. Thereafter, the mixture was cooled to room temperature, to which Na2CO3 (1.3 g, 11.8 mmol) was added before further refluxing for 10 h. After cooling to room temperature, the mixture was filtered and evaporated to remove ethanol. The residue was dissolved in CHCl3, and washed with water and saturated brine in turn, and then dried over anhydrous Na2SO4. After concentration and purification with silica gel column chromatography (using CHCl3/CH3OH (60/1) as an eluent), Intermediate 4A (1.0 g, 24% yield) as a brown solid was obtained. MS[M]+=449.4 m/e; 1H-NMR (400 MHz, DMSO-d6), delta 7.987.96 (m, 2H), 7.467.38 (m, 3H), 7.06 (d, 2H), 6.81 (d, 2H), 2.702.61 (m, 2H), 2.602.51 (m, 2H), 2.36 (s, 3H).

The synthetic route of 43204-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIJING MOLECULE SCIENCE AND TECHNOLOGY CO., LTD.; US2007/259883; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 89359-54-6, name is 9-Bromo-1-nonene, 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. SDS of cas: 89359-54-6

10470] To a flame dried 500 mE RB flask, freshly activated Mg turnings (9 g) were added and the flask was equipped with a magnetic stir bar, an addition thnnel and a reflux condenser. This set-up was degassed and flushed with argon and 100 mE of anhydrous ether was added to the flask via syringe. The bromide 3 (51.3 g, 250 mmol) was dissolved in anhydrous ether (100 mE) and added to the addition thnnel. About 5 mE of this ether solution was added to the Mg turnings while stirring vigorously. An exothermic reaction was noticed (to confirmlaccelerate the Grignard reagent formation, 5 mg of iodine was added and immediate decolorization was observed confirming the formation of the Grignard reagent) and the ether started refluxing. The rest of the solution of the bromide was added dropwise while keeping the reaction under gentle reflux by cooling the flask in watet Afier the completion of the addition the reaction mixture was kept at 35C. for 1 hour and then cooled in ice bath. Ethyl formate (9 g, 121 mmol) was dissolved in anhydrous ether (100 mE) and transferred to the addition thnnel and added dropwise to the reaction mixture with stirring. An exothermic reaction was observed and the reaction mixture started refluxing. After the initiation of the reaction the rest of the ethereal solution of formate was quickly added as a stream and the reaction mixture was stirred for a further period of 1 h at ambient temperature. The reaction was quenched by adding 10 mE of acetone dropwise followed by ice cold water (60 mE). The reaction mixture was treated with aq. H2S04 (10% by volume, 300 mE) until the solution became homogeneous and the layers were separated. The aq. phase was extracted with ether (2×200 mE). The combined ether layers were dried (Na2 SO4) and concentrated to afford the crude product which was purified by colunm (silica gel, 0-10% ether in hexanes) chromatography. The product fractions were evaporated to provide the pure product 11 as a white solid (30.6 g, 90%). ?H NMR (400 MHz, CDC13) oe 7.26 (s, 1H), 5.81 (ddt, J=16.9, 10.2, 6.7 Hz, 8H), 5.04-4.88 (m, 16H), 3.57 (dd, J=7.6, 3.3 Hz, 4H), 2.04 (q, J=6.9 Hz, 16H), 1.59(s, 1H), 1.45 (d,J=7.5 Hz, 8H), 1.43-1.12 (m, 94H), 0.88 (t, J=6.8 Hz, 2H). ?3C NMR (101 MHz, cdcl3) oe 139.40, 114.33, 77.54, 77.22, 76.90, 72.21,37.70,34.00,29.86,29.67,29.29,29.12,25.85.

The synthetic route of 9-Bromo-1-nonene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALNYLAM PHARMACEUTICALS, INC.; MANOHARAN, Muthiah; MAIER, Martin; JAYARAMAN, Muthusamy; MATSUDA, Shigeo; NAIR, Jayaprakash K.; RAJEEV, Kallanthottathil G.; AKINC, Akin; BAILLIE, Thomas A.; (104 pag.)US2016/9637; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

61613-22-7, name is 2-Bromo-N-phenylaniline, 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. Computed Properties of C12H10BrN

After dissolving 10 g of 2-bromo-N-phenylphenylamine in 100 ml of tetrahydrofuran, the reaction temperature was lowered to -78 C,Slowly add 20 ml of 2.5 M butyllithium and stir for 1 h. 11 g of benzophenone was dissolved in 100 ml of tetrahydrofuran and slowlyAfter dropping, the temperature was increased to room temperature and stirred for 12 h. After the reaction has ended, distilled water and methylene chloride will be usedRow extraction and drying by anhydrous magnesium sulfate followed by filtration under reduced pressure gave the solid which was dissolved in 100 ml of acetic acid, 7 ml of sulfuric acid was added dropwise and the mixture was reflux-stirred. After the reaction was completed, the mixture was extracted with distilled water and methylene chlorideThe resulting solid was purified by column chromatography to give Intermediate B-1 (7.1 g, yield 53%).

The synthetic route of 61613-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Liu Xiqing; Cai Hui; (24 pag.)CN107400085; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary