Category: 76153-06-5

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. 76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, A new synthetic method of this compound is introduced below., Recommanded Product: 76153-06-5

The compound was synthesized starting from (S)-4-phenyloxazolidin-2-one (1 equiv., 0.326 g, 2 mmol), 5-bromo-3-methylbenzene-1,2-diamine (1 equiv., 0.402 g, 2 mmol), copper(I) iodide (0.1 equiv., 0.038 g, 0.2 mmol), cesium fluoride (2 equiv., 0.605 g, 4 mmol), cyclohexane-1,2-diamine (0.1 equiv., 0.024 mL, 0.2 mmol). The solids were given together in a reaction flask and the flask was purged with argon. A solution of cyclohexane-1,2-diamine in 10 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%).

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

These common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-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. Quality Control of 5-Bromo-3-methylbenzene-1,2-diamine

A mixture of 5-bromo-3-methylbenzene-l , 2-diamine (2.5 mmol, 0.5 g) , was suspended in trimethylorthoformate (1042) (34 mL) and para-toluene sulfonic acid monohydrate (0.17 g) was added. The suspension was heated at 115 C for 1.5 hours, and then cooled to room temperature. The mixture was diluted with dichloromethane and washed with (1043) saturated sodium bicarbonate solution and brine. The organic extracts were combined, passed through a phase separator cartridge and concentrated under reduced pressure to afford the crude title compound as a brown solid (0.78 g, >100%) which was used without further purification.

The synthetic route of 5-Bromo-3-methylbenzene-1,2-diamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; SAITO, Tetsuji; HIGASHINO, Masato; KAWAHARADA, Soichi; LEWIS, Arwel; CHAMBERS, Mark Stuart; RAE, Alastair; HIRST, Kim Louise; HARTLEY, Charles David; WO2015/115673; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 76153-06-5, These common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-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.

EXAMPLE 375-Methyl-7-r3-(piperidin-l-ylmethyl)phenyl]quinoxalineGlyoxal (10 drops of a 40% solution in water) was added to a solution of 5- bromo-2,3-diaminomethylbenzene (80 mg, 0.4 mmol) in ethanol (3 mL). The mixture was stirred and left to stand at r.t. for 1 h. The mixture was partitioned between water and EtOAc (20 mL each), and the organic phase was dried (MgSO4) and concentrated in vacuo. The residue was dissolved in DME (1.2 mL), and 3-(piperidin-l-ylmethyl)phenyl- boronic acid pinacol ester hydrochloride (135 mg, 0.4 mmol), 2M aqueous sodium carbonate solution (0.6 mL, 0.9 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) were added. The mixture was heated to 1200C in a sealed tube, under microwave irradiation, for 20 minutes. The mixture was partitioned between water and EtOAc (2 mL each), and the organic phase was concentrated in vacuo. The residue was purified by preparative HPLC to give the title compound (5 mg, 4% over the two steps) as a pale yellow-brown gum. delta? (CDCl3) 8.87 (d, IH), 8.85 (d, IH), 8.17 (s, IH), 7.93 (s, IH), 7.72 (s, IH), 7.65 (d, IH), 7.46 (t, IH), 7.39 (d, IH), 3.58 (s, 2H), 2.88 (s, 3H), 2.34-2.52 (m, 4H), 1.51-1.68 (m, 4H), 1.39-1.51 (m, 2H). LCMS (ES+) 318 (M+H)+, RT 2.43 minutes.

Statistics shows that 5-Bromo-3-methylbenzene-1,2-diamine is playing an increasingly important role. we look forward to future research findings about 76153-06-5.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, 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. Product Details of 76153-06-5

b 7-Bromo-5-methyl-1,2,3,4-tetrahydroquinoxalin-2,3-dione 13.05 g (64.9 mmol) of 5-bromo-2,3-diaminotoluene and 6.42 g (1.1 eq.) of oxalic acid are stirred under reflux for 16 hours in 2N hydrochloric acid. The mixture is cooled, and the solid is filtered off and washed with water. The title compound is obtained as a brown solid. 1 H-NMR (250 MHz, DMSO); delta==11.98, 11.32 (2s, 2NH), 7.13 (s, 2H), 2.33 (s, Me).

The synthetic route of 76153-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Novartis AG; US6117873; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 76153-06-5, A common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

Isothiocyanatomethane (0.055 g, 0.746 mmol) in N,N-dimethylformamide (1.0 mL) was added dropwise slowly to a stirred solution of 5-bromo-3-methylbenzene-l,2-diamine (0.150 g, 0.746 mmol) in N,N-dimethylformamide (1.5 mL) at 0 0C. The cold bath was removed, the reaction mixture was capped and stirred at room temperature for 48 h. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.157 g, 0.821 mmol) was added and the reaction mixture capped and heated at 40 0C overnight. The resulting mixture was diluted with methanol, filtered and purified using reverse-phase preparatory HPLC (10-50 % acetonitrile + 0.1 % TFA in H2O + 0.1 % TFA, over 30 min). Fractions containing the desired product were combined and most of the solvent removed under reduced pressure. Acetonitrile was added and the resulting mixture loaded on a Strata ion exchange column. The column was washed successively with water, acetonitrile, methanol and 5 % ammonium hydroxide in methanol. The product eluted with the 5% ammonium hydroxide in methanol and was concentrated under reduced pressure and dried under high vacuum to give the desired product (0.128 g, 0.53 mmol, 72 % yield) as a slightly yellow waxy solid. MS (ESI) m/z 240 [M]+, 242 [M+2]+.

The synthetic route of 76153-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; ELSNER, Jan; HARRIS, Roy, L.; LEE, Branden; MORTENSEN, Deborah; PACKARD, Garrick; PAPA, Patrick; PERRIN-NINKOVIC, Sophie; RIGGS, Jennifer; SANKAR, Sabita; SAPIENZA, John; SHEVLIN, Graziella; TEHRANI, Lida; XU, Weiming; ZHAO, Jingjing; PARNES, Jason; MADAKAMUTIL Loui; FULTZ Kimberly; NARLA, Rama K.; WO2010/62571; (2010); 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 76153-06-5 as follows. Application In Synthesis of 5-Bromo-3-methylbenzene-1,2-diamine

7-bromo-5-methylquinoxaline. To a solution of 5-bromo-3-methylbenzene-1,2-diamine (Bioorg. Med. Chem. 2000, 2591.) (3.63 g, 18.05 mmol) in ethanol (50 ml) was added glyoxal 40 wt. % in water (8.0 ml, 69.7 mmol). The mixture was heated to reflux for 1.5 hours and an aliquot was removed, concentrated and analyzed by LC/MS. Many overlapping peaks were observed, including a major peak corresponding to desired mass 225 ([M+H]+ for 81Br isotope). The mixture was removed from heat and allowed to stir overnight. Reflux was resumed for 1.5 hours and another aliquot was taken. LC/MS showed a higher ratio of desired to other peaks by integration. Analysis after 6 hours showed no appreciable change. The mixture was concentrated to remove most of the ethanol then diluted with water and dichloromethane. The layers were shaken and separated and the aqueous portion was extracted 2* with dichloromethane. Combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give 4.96 g of a black thick residue. The crude material was purified via column chromatography (SiO2) eluding with 10% ethyl acetate/hexane to give the product as a white solid (1.70 g, 7.62 mmol, 42%). 1H NMR (400 MHz, MeOD) delta ppm 8.80-8.84 (2H, m), 8.07 (1H, d, J=2.27 Hz), 7.39 (2H, dd, J=9.07, 5.29 Hz), 7.34 (1H, s), 7.07 (2H, t, J=8.81 Hz), 5.47 (1H, q, J=6.30 Hz), 3.47 (1H, d, J=8.81 Hz), 3.29-3.31 (1H, m), 2.75-2.92 (2H, m), 2.34 (3H, s), 2.31-2.55 (3H, m), 2.07-2.29 (2H, m), 1.96-2.06 (1H, m), 1.36 (3H, d, J=6.30 Hz). Mass 225 [M+H]+ (81Br).

According to the analysis of related databases, 76153-06-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/18163; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary