Category: bromides-buliding-blocks

Synthetic Route of 64248-56-2, A common heterocyclic compound, 64248-56-2, name is 2-Bromo-1,3-difluorobenzene, molecular formula is C6H3BrF2, 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 A-22 4-(2,6-Difluoro-phenyl)-1H-indole To a mixture of 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole (11.34 g, 46.6 mmol), and 1-bromo-2,6-difluorobenzene (9 g, 46.6 mmol) in 1,2-dimethoxyethane (204 mL) were added Palladium catalyst Pd(PPh3)4 (1.62 g, 1.4 mmol) and the freshly prepared sodium carbonate solution (15.19 g in 66 mL of water). The system was degassed and then charged with nitrogen. The degas procedure was repeated for three times. The mixture was stirred under nitrogen at 110 C. oil bath for overnight. TLC showed the completion of the coupling reaction. The mixture was cooled to room temperature, diluted with ethyl acetate, and separated from water layer. The ethyl acetate solution was washed with brine, and dried over Na2SO4. After filtration, the solvents were evaporated, and the crude product was purified by a silica gel column to give 9.77 g (91%) of 4-(2,6-difluoro-phenyl)-1H-indole.

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; Sugen, Inc.; US2003/69297; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4549-33-1, 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. 4549-33-1, name is 1,9-Dibromononane, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of 6-(4-chlorophenyl)-1-methyl-8-(1H-pyrazol-4- yl)spiro[benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-4,1′-cyclopropane] (59-2) (100 mg, 249 mumol) in DMF(1.5 mL) was added Cs2CO3 (121 mg, 373 mumol) and 1,9-dibromononane (85.2 mg, 298 mumol) . The mixture was stirred for 4h at 30 C. Water(30 mL) and EA(30 mL*2) were added. The Combined organic layers was dried over Na2SO4 and concentrated, purified with prep- TLC (EA=100%) to give 8-(1-(9-bromononyl)-1H-pyrazol-4-yl)-6-(4-chlorophenyl)-1- methylspiro[benzo[f][1,2,4]triazolo[4,3-a][1,4]diazepine-4,1′-cyclopropane] (113-1) (39.2 mg, 26.1 %) as an oil. LCMS (ES+): m/z= 605 [M + H]+

The chemical industry reduces the impact on the environment during synthesis 1,9-Dibromononane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; C4 THERAPEUTICS, INC.; PHILLIPS, Andrew, J.; NASVESCHUK, Chris, G.; HENDERSON, James, A.; LIANG, Yanke; FITZGERALD, Mark, E.; MICHAEL, Ryan, E.; (790 pag.)WO2017/197056; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 112734-22-2, 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 112734-22-2 as follows.

General procedure: To a stirred solution of N-(t-butoxycarbonyl)glycine (1 mmol) in CH2Cl2 (10 mL) was added CDI (1.1 mmol), and the resulting mixture was stirred at room temperature for 1 h. To the resulting mixture was added amine (1 mmol), and the reaction mixture was stirred at room temperature for 24 h. The solvent was removed under reduced pressure, and the residue was chromatographed on silica gel (20 g, hexane : acetone = 6 : 1 ~ 3 : 1) to give the corresponding amide.

According to the analysis of related databases, 112734-22-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mori, Hisashi; Wada, Ryogo; Li, Jie; Ishimoto, Tetsuya; Mizuguchi, Mineyuki; Obita, Takayuki; Gouda, Hiroaki; Hirono, Shuichi; Toyooka, Naoki; Bioorganic and Medicinal Chemistry Letters; vol. 24; 16; (2014); p. 3732 – 3735;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-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. Formula: C6H3BrF2

General procedure: To an oven-dried 25 mL Schlenk tube containing a stirring bar was added 4.5 mg Pd(OAc)2 (0.02 mmol), 15.7mg nBuPAd2 (0.44 mmol), 2-bromofluorobenzene (0.50 mmol), salicylaldehyde (0.50 mmol), potassium carbonate (1.0 mmol). The Schlenk tube was vacuumed and then purged with argon before DMF (2.0 mL) was injected using a syringe. Afterwards the Schlenk tube in the ice bath was degassed by evacuation and back fillingwith argon three times. The reaction mixture was then stirred for 12 h at 120 C. After the reaction was complete,the reaction mixture was diluted with water (5 mL), extracted with ethyl acetate (3 x 10 mL) and dried withanhydrous Na2SO4. After filtration and addition of silica gel into the solution, the organic solvent was reduced evaporated. The crude product was purified by column chromatography using ethyl acetate/n-pentane.

The synthetic route of 1-Bromo-2,5-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shen, Chaoren; Wu, Xiao-Feng; Synlett; vol. 27; 8; (2016); p. 1269 – 1273;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 615-54-3, These common heterocyclic compound, 615-54-3, name is 1,2,4-Tribromobenzene, 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.

[00149] A suspension of compound 1 (27.0 g, 85.7mmol), potassium vinyltrifluoroborate (compound 4) (41.4 g, 0.31 mol), PdCI2 (0.76g, 4.3mmol), Cs2C03 (125.6 g, 0.39 mol) and PPh3 (3.38g, 12.9mmol) in a mixture of THF and water (400ml_, THF/H20 9:1 ) was heated at reflux for 17h under a nitrogen atmosphere. The reaction was cooled to room temperature and the solvent removed by evaporation. The residue obtained was diluted with water (300ml_) and extracted with ethyl acetate (100ml_ x 3). The combined organic extracts were washed with water (200mL) and brine (100ml_), dried (Na2S04) and concentrated to give the crude product, which was purified by column chromatography (neat petroleum ether), illustrated below, to afford compound 5 (1 1.40g, 85%) as an oil.

The synthetic route of 615-54-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOULOS & COOPER PHARMACEUTICALS PTY LTD; BOULOS, Ramiz; FEUTRILL, John; (105 pag.)WO2017/27933; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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.

Water (11.38 mL) was added to a solution consisting of 3-bromo-4-fluoroaniline (10 g, 53 mmol), sodium 3-nitrobenzenesulfonate (21 g, 95 mmol), and propane-1,2,3-triol (14 g, 0.15 mol). The resultant mixture was carefully treated with concentrated H2SO4 (21.1 mL), and then heated to 150 C. with stirring for 2 h before cooling to room temperature. The resultant mixture was carefully neutralized with 5 N sodium hydroxide, filtered through a pad of diatomaceous earth, and the pad was washed with dichloromethane (50 mL). The resultant mixture was extracted with dichloromethane (100 mL*3) and the combined organic extracts were dried over Na2SO4, filtered, and the filtrate concentrated to give a crude product, which was purified by FCC (petroleum ether: ethyl acetate=3:1) to afford the compounds 62a and 62a-1 (9.5 g, 80%). LCMS (ESI): RT=0.64, 0.68 min, mass calcd. for C9H5BrFN 224.96, m/z found 227.6 [M+H]+. 1H NMR (400 MHz, CDCl3) delta 8.96-8.87 (m, 2H), 8.55 (d, J=8.8 Hz, 1H), 8.39 (d, J=6.8 Hz, 1H), 8.15-8.07 (m, 2H), 7.60-7.42 (m, 4H). A mixture of 5-bromo-6-fluoroquinoline, 62a and7-bromo-6-fluoroquinoline, 62a-1 (10 g, 22 mmol), (diphenylmethylene)hydrazine (4.3 g, 22 mmol), 2,2?-bis(diphe- nylphosphino)-1,1?-binaphthyl (1.4 g, 2.2 mmol), palladium (II) acetate (0.50 g, 2.2 mmol), t-l3uONa (6.4 g, 66 mmol), and 1,4-dioxane (150 mE) was stirred at 1000 C. for 16 h. The suspension was filtered through a pad of diatomaceous earth and the pad was washed with ethyl acetate (30 mE). The filtrate was concentrated to dryness under reduced pressure to give a crude product, which was added into water (30 mE). The resultant mixture was extracted with ethyl acetate (50 mEx3). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and the filtrate concentrated to dryness under reduced pressure to afford the crude product, which was purified by FCC (petroleum ether:ethyl acetate=3:1) to afford compounds 62b and 62b-1 (5 g, 33%). ECMS (ESI): RT=0.68 mm, mass calcd. for C22H,6FN3 341.13, mlz found 341.9 [M+H]. Concentrated HC1 (10 mE) was added to a solution consisting of 5-(2-(diphenylmethylene)hydrazinyl)-6-fluo- roquinoline, 62b and 7-(2-(diphenylmethylene)hydrazinyl)- 6-fluoroquinoline, 62b-1 (5.0 g, 7.3 mmol) and EtOH (3 mE). The resultant solution was stirred at room temperature for 16 h. The resultant mixture was treated with water (30 mE) and extracted with dichloromethane (30 mEx3). Theaqueous phase was basified with 5 M NaOH to pH 12. Thesuspension was filtered and the collected solids were washedwith water (20 mE) and dried under reduced pressure toafford compounds 62c and 62c-1 (1.2 g, 46%). ECMS (ESI):RT=1.24 mm, mass calcd. for C9H8FN3 177.07, mlz found178.1 [M+H].

The synthetic route of 656-64-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 399-94-0, These common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-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.

Method B:To a solution of 1-bromo-2,5-difluorobenzene (42.2 g, 0.218 mol) in toluene (85 mL) at -10 to -5 C. was added iPrMgCl/LiCl solution (1.0 M in THF, 240 mL, 0.24 mol) dropwise over 1.5 h. The reaction solution was then aged for 30 min at -10 to -5 C.In a separate vessel, Weinreb amide 4 (28 g, 0.109 mol) was dissolved in THF (112 mL), cooled to 15 C. and then charged to the above Grignard solution over about 30 min, while the internal temperature was maintained at -10 to -5 C. The reaction mixture was then warmed to 20 C. over 1 h, and aged for additional 1 h at 20 C. for complete reaction. The reaction mixture was quenched with an aqueous HCl solution (32.5 g of concentrated hydrochloric acid in 110 mL of water) at 0 to 10 C. over 30 min. The organic phase was washed with 10% NaCl solution (200 mL×2). The organic phase was solvent switched to iPrOH (final volume about 270 mL) and water (380 mL) was added over 1 h at 20 C. Solids were filtered and washed with 40% iPrOH in water (60 mL×2). The wet cake was dried under vacuum at 45 C.1H-NMR (500 MHz, CDCl3): delta 7.56 (m, 1H), 7.25 (m, 1H); 7.15 (m, 1H), 5.67 (d, J=7.3 Hz, 1H), 5.24 (m, 1H), 2.91 (m, 1H), 2.68 (m, 1H), 2.00 (t, J=2.43, 1H), 1.45 (s, 9H). 13C-NMR (125 MHz, CDCl3): delta 159.03 (dd, J=245.5, 1.8 Hz), 157.4 (d, J=248.0 Hz), 124.6 (dd, J=15.4, 6.2 Hz), 122.2 (dd, J=24.6, 9.8 Hz), 118.4 (dd, J=27.1, 8.0 Hz), 117.6 (DD, J=25.2, 3.7 Hz), 80.4, 78.4, 72.1, 57.9 (d, J=7.5 Hz), 28.5, 22.3.

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xu, Feng; Kim, Mary M.; Kohmura, Yoshinori; Sladicka, Tricia; Rosen, Jonathan D.; Zacuto, Michael J.; US2009/187028; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 58534-95-5, name is 3-Bromo-2-fluoroaniline, 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 58534-95-5, Product Details of 58534-95-5

[0179] To a solution of 3-bromo-2-fluoroaniline (0.5 g, 2.63 mmol) in Pyridine (20 mL) was added propane-1-sulfonyl chloride (3.75 g, 26.3 mmol) at rt, the reaction was stirred at 60C for 3h under N2, after the reaction was completed, the solvent was removed. The residue was purified on silica gel column chromatography (PE/EtOAc = 10/1) to afford N-(3- bromo-2-fluorophenyl)propane-1-sulfonamide (364 mg, 47% yield) as a yellow solid (the product has no MS).

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-2-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ABM THERAPEUTICS, INC.; CHEN, Chen; (154 pag.)WO2019/60611; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 58534-95-5, These common heterocyclic compound, 58534-95-5, name is 3-Bromo-2-fluoroaniline, 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.

To a stirred solution of N-Boc-trans-4-fluoro-proline (25 g, 1 equiv), 3-bromo-2- fluoroaniline (14.5 mL, 1.2 equiv) and HATU (53 g, 1.3 equiv) in DMF (250 mL) was added DIPEA (37 mL, 2 equiv) and the resulting solution was stirred at room temperature under an atmosphere of nitrogen. The reaction mixture was poured into water and filtered and the collected solid was washed with excess water. The solid was dissolved in DCM and washed with 10% NaHCCb, 1.5 N HC1, and brine. The solvent was removed under vacuum, hexane was added, and the precipitated solid was collected by filtration to afford the title product (27 g).

Statistics shows that 3-Bromo-2-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 58534-95-5.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1422-54-4, 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. 1422-54-4, name is 2-Bromo-6-fluorotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 187 6-(3-Fluoro-2-methylphenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 287, structure 4 of Scheme II, where R1 =3-fluoro-2-methylphenyl) This compound was prepared by General Method 2 (EXAMPLE 9) from Compound 9 (50 mg, 0.158 mmol) and 2-bromo-6-fluorotoluene (60 mg, 0.315 mmol). Purification by flash chromatography on silica gel (20g) using 5% EtOAc:hexanes afforded 6 mg(14%) of Compound 287 as a yellow oil. Data for Compound 287: 1 H NMR (400 MHz, acetone-d6) 7.20 (m, 1H), 7.02 (m, 1H), 6.98 (m, 2H), 6.91 (m, 1H), 6.56 (d, J=8.0, 1H), 5.37 (s, 1H), 5.37 (s, 1H), 5.29 (br s, 1H), 2.19 (s, 3H), 1.98 (s, 3H), 1.28 (s, 6H).

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, 2-Bromo-6-fluorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5693647; (1997); A;,
Bromide – Wikipedia,
bromide – Wiktionary