Category: 153505-37-4

Application of 153505-37-4, 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. 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 15: Step ITo a cold (0-4 C) solution of 4-bromo-5-fluoro-benzene-1 ,2-diamine (1 g, 4.877 mmol) and (2S)-1 -tert-butoxycarbonylpyrrolidine-2-carboxylic acid (Boc-Pro-OH) (1.050 g, 4.877 mmol) in DMF (9.754 mL) are sequentially added HATU (2.040 g, 5.365 mmol) and 2,4,6-collidine (886.5 mg, 966.7 mul_, 7.316 mmol). The reaction mixture is slowly warmed up to rt, stirred overnight, and diluted with water (20 mL). The resulting suspension is extracted with EtOAc(3 x 25 mL), and the combined extracts are washed with saturated bicarbonate solution, and brine. The organic phase is dried over sodium sulfate, and concentrated under vacuum to give crude amide (2.35 g, contaminated with 2,4,6-collidine). The residue is dissolved in acetic acid (15 mL), stirred at 50 C for 8 h, and concentrated to dryness. The residue is diluted with ethyl acetate (25 mL), washed with aq. NaHCO3 solution, and brine. The organic phase is dried over sodium sulfate, concentrated under vacuum and the residue is purified by silica gel chromatography (ethyl acetate/hexanes,40 to 60 %) to give 15 (1.74 g) as light brown solid.1 H NMR spectra in CDCl 3 and CD 3 OD showed 1.2:1 and 2:1 ratio of isomeric mixture (exchange of imidazole nitrogen) .19F spectra also showed mixture of two isomers. 1H NMR (400 MHz, CDCl3, 1.2:1 ratio of isomers): Peaks for the major isomer, delta [ppm] 7.86 (d, J = 6.2, 1 H), 7.45 (d, J = 9.2, 1 H), 6.77(s, 0.35 H), 5.02 (m, 1 H), 3.41 (m, 2 H), 2.2-1.9 (m, 2 H), 1.49 (s, 3 H). LC/MS: m/z = 303.78 (M-100+H+). 19F NMR (400 MHz, CDC13), delta [ppm] -113.4 (t), -115.7 (t).

The synthetic route of 4-Bromo-5-fluorobenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; HENDERSON, James A.; MAXWELL, John; VAILLANCOURT, Louis; MORRIS, Mark; GREY, JR., Ronald; GIROUX, Simon; KONG, Laval Chan Chun; DAS, Sanjoy Kumar; LIU, Bingcan; POISSON, Carl; CADILHAC, Caroline; BUBENIK, Monica; REDDY, T. Jagadeeswar; FALARDEAU, Guy; YANNOPOULOS, Constantin; WANG, Jian; PEREIRA, Oswy Z.; BENNANI, Youssef L.; PIERCE, Albert C.; BHISETTI, Govinda Rao; COTTRELL, Kevin M.; MARONE, Valerie; WO2011/9084; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, 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 153505-37-4, Application In Synthesis of 4-Bromo-5-fluorobenzene-1,2-diamine

Preparation 38 5-Bromo-6-fluorobenzo[c][1,2,5]thiadiazole 4-Bromo-5-fluorobenzene-1,2-diamine (500 mg, 2.4 mmol) was dissolved in 20 mL chloroform, treated in portions with thionyl chloride (580 mg, 4.9 mmol) and heated to reflux for 20 h. After cooling the mixture was diluted with 60 mL ethyl acetate, washed with 15 mL water, 15 mL saturated NaCl, dried (Na2SO4) and concentrated under vacuum. The material was chromatographed on silica with a 0-30% ethyl acetate-hexane gradient to give the title compound as a white solid (425 mg, 76%): mp 79-82 C.; 1H NMR (400 MHz, CDCl3) delta 8.33 (d, J=6.7 Hz, 1H), 7.72 (d, J=8.3 Hz, 1H); 19F NMR (376 MHz, CDCl3) delta -102.91; EIMS m/z 232.

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Reference:
Patent; Dow AgroSciences, LLC; Eckelbarger, Joseph D.; Siddall, Thomas L.; Satchivi, Norbert M.; Schmitzer, Paul R.; US2014/274702; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C6H6BrFN2

4-bromo-5-fluorobenzene-1,2-diamine (5.00 g, 24.4 mmol) was solubilised in 1 ,4-dioxane (200 ml). 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (7.43 g, 29.3 mmol), potassium acetate (12.0 g, 122 mmol) and dichlorobis(tricyclohexylphosphine)palladium(ll) (900 mg, 1 .22 mmol) were added and the mixture was stirred overnight at 1 10C. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica gel to give 3.23 g (90 % purity, 47 % yield) of the title compound. LC-MS (Method 2): Rt = 0.75 min; MS (ESIpos): m/z = 253 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) _ [ppm]: 1.066 (0.59), 1 .156 (2.87), 1 .230 (16.00), 5.191 (1.07), 6.172 (1.00), 6.200 (1.04), 6.739 (0.89), 6.755 (0.89).

The synthetic route of 153505-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LEFRANC, Julien; MENGEL, Anne; SCHULZE, Volker; CHRIST, Clara; PRINZ, Florian; WENGNER, Antje, Margret; STOeCKIGT, Detlef; BOeMER, Ulf; BADER, Benjamin; (288 pag.)WO2017/207534; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 153505-37-4, These common heterocyclic compound, 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, 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 solution of 4-bromo-5-fluorobenzene-1,2-diamine (4.50 g, 21.95 mmol), (S)-2-((tert-butoxycarbonyl)amino)-3 ,3-dimethylbutanoic acid (5.08 g, 21.95 mmol), DIPEA (3.83 mL, 21.95 mmol) in CH2C12 (200 mL) at 0 C was added HATU (8.35 g, 21.95 mmol). The reaction mixture was stirred for 18 h at RT. After which, water (500 mL) was added into the reaction mixture and extracted with ethyl acetate (3 x100 mL). The organic layer was washed with brine, dried (Na2SO4) and concentrated to afford Bla and/or ite regioisomer (10.0 g) as brown liquid. Crude was taken fornext step without further purification. LC/MS: Anal. Calcd. for [M+Hj mz C17H26BrFN3O3: 420.11; found 420.1.

The synthetic route of 153505-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; FRENNESSON, David B.; HEWAWASAM, Piyasena; LOPEZ, Omar D.; NGUYEN, Van N.; SAULNIER, Mark G.; TU, Yong; WANG, Alan Xiangdong; WANG, Gan; XU, Ningning; NIMJE, Roshan Yadavrao; RAHAMAN, Hasibur; GUPTA, Samayamunthula Venkata Satya Arun Kumar; MEANWELL, Nicholas A.; BELEMA, Makonen; (107 pag.)WO2017/23631; (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. 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 153505-37-4

The compound was synthesized starting from (S)-4-phenyloxazolidin-2-one (1 equiv., 0.328 g, 2 mmol), 4-bromo-5-fluorobenzene-1,2-diamine (1 equiv., 0.412 g, 2 mmol), copper(I) iodide (0.1 equiv., 0.040 g, 0.2 mmol), cesium fluoride (2 equiv., 0.608 g, 4 mmol), cyclohexane-1,2-diamine (0.1 equiv., 0.024 mL, 0.2 mmol). The dried solids were given together in a reaction flask and the flask was purged with argon. A solution of cyclohexane-1,2-diamine in 4 mL dioxane was added to the flask. The reaction was stirred at 95 C. for 48 hours, before the reaction was cooled down to 45 C. and filtered through a pad of CELITE. The pad was washed with warm dichloromethane and the solution was concentrated under reduced pressure. The intermediate product was purified via FPLC using a chloroform-methanol gradient (0?10%, product elutes at about 5%).Yield: 0.078 g (13.6%)

According to the analysis of related databases, 153505-37-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROBIODRUG AG; US2011/92501; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 153505-37-4, A common heterocyclic compound, 153505-37-4, name is 4-Bromo-5-fluorobenzene-1,2-diamine, molecular formula is C6H6BrFN2, 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.

2-Amino-4-bromo-5-fluoroaniline (9.2 g, 45 mmol) was dissolved in acetic acid (190 ml) and water (260 ml) before sodium nitrite (3.1 g, 45 mmol) in 10 mL of water was added dropwise. The reaction was stirred at room temperature for 1 hour before the solution was cooled to 0 C and ammonium hydroxide was added to adjust the pH to ~11. The mixture was extracted with EtOAc (3 x 500 mL), and the combined organics were dried over sodium sulfate, filtered, and concentrated to a brown solid (9.0 g, 71 %). MS (m/z) 215.9, 217.9 (M+, M+2+). 5-bromo-6-fluoro-1H-1,2,3-benzotriazole (1.0 g, 4.6 mmol), copper(I) iodide (88 mg, 0.46 mmol), and sodium iodide (2.8 g, 19 mmol) were added to a flask which was subsequently purged with argon. 1,4-Dioxane (7.0 ml) was added followed by N,N’-ethylenediamine (0.10 ml, 0.93 mmol). The reaction was heated to 120 C overnight. It was cooled to room temperature and partitioned between water and EtOAc. The organics were collected and the aqueous layer was back-extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered, and concentrated (420 mg, 35 %). MS (m/z) 263.9 (M+H+).

The synthetic route of 153505-37-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GlaxoSmithKline Intellectual Property Development Limited; BURY, Michael, Jonathan; CASILLAS, Linda, N.; CHARNLEY, Adam, Kenneth; DEMARTINO, Michael, P.; DONG, Xiaoyang; HAILE, Pamela, A.; HARRIS, Philip, Anthony; LAKDAWALA SHAH, Ami; KING, Bryan, W.; MARQUIS, Robert, W., Jr.; MEHLMANN, John, F.; ROMANO, Joseph, J.; SEHON, Clark, A.; EIDAM, Patric; EP2566477; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary