Tag: M.W=200-300

Synthetic Route of 103273-01-4,Some common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

Step 2: Synthesis of 2-amino-3′,5-di-t-butylbiphenyl 3-t-butylphenylboronic acid (4.0 g, 22.4 mmol), 2-bromo-4-t-butylaniline (4.3 g, 18.7 mmol), palladium(II) acetate (0.11 g, 0.468 mmol), triphenylphosphine (0.5 g, 1.8 mmol) and was added 2 M solution of potassium carbonate in 25 of ethylene glycol dimethyl ether in the 36 . The reaction mixture was heated under reflux for 18 hours. Cool the reaction to room temperature, and separating the aqueous phase from the organic phase. The aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered and concentrated. It was purified by column chromatography using 20% ethyl acetate and hexane the crude product as an eluent. Collected as a pure product of 2-amino-3 ‘, 5-di -t- butyl biphenyl (3.0 g, 57% yield) of a white solid, and its NMR is consistent with the proposed structure.

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-4-(tert-butyl)aniline, its application will become more common.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; NOLIS, DAVID B; LIN, CHOOK; MCKINSEY, PETER BODON; CHAI, CHUI LEE; WALTERS, ROBERT W; PIERS, SCOTT A; BROWN, CORY S; IGOR, WALTER H; (101 pag.)KR2016/30582; (2016); A;,
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. 811711-33-8, name is 1,2-Dibromo-3-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 811711-33-8

A mixture of 2.5 g (12.23 mmol) of 7,8-difluoro-2-methylquinolin-3-amine and 3.32 g (12.84 mmol) of 1 ,2- dibromo-3-fluorobenzene together with 11.95 mg (36.69 mmol) of cesium carbonate and 708 mg (1.22 mmol) of 9,9-dimethyl-9H-xanthene-4,5-diyl)bis-(diphenylphosphane [Xantphos] in 70 mL of 1 ,4-dioxane was degassed with argon for 30 minutes. 896 mg (0.97 mmol) of tris(dibenzylideneacetone)pailadium(0) was added and the reaction mixture was heated at reflux for 26 hours. The cooled reaction mixture was filtered over a silica gel pad, and the pad washed by ethyl acetate. The organic phase was concentrated under vacuo and purified by column chromatography on silica gel (300 g cartridge – gradient n-heptane/ethyl acetate) to yield 2.31 g (49%) of N-(2-bromo-3-fluorophenyl)-7,8-difluoro-2-methylquinolin-3-amine. LogP = 3.28. Mass (M+H) = 367

According to the analysis of related databases, 811711-33-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; CRISTAU, Pierre; DESBORDES, Philippe; DUFOUR, Jeremy; GOURGUES, Mathieu; LAMPRECHT, Sybille; LOQUE, Dominique; MEISSNER, Ruth; NAUD, Sebastien; THOMAS, Vincent; (90 pag.)WO2020/79173; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 608-30-0,Some common heterocyclic compound, 608-30-0, name is 2,6-Dibromoaniline, molecular formula is C6H5Br2N, 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-chloro-5-methoxyphenylboronic acid (1.25 g, 6.71 mmol), 2,6-dibromoaniline (1.851 g, 7.38 mmol), sodium carbonate (6.71 mL, 13.41 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.465 g, 0.40 mmol) were dissolved in dioxane (10 mL), degassed and sealed into a microwave tube. The reaction was heated to 1500C for 1 hour in the microwave reactor and cooled to room temperature.The reaction mixture was poured into saturated aqueous NH4CI solution (100 mL), extracted with EtOAc (100 mL), and the organic layer was washed with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford an orange oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford 3-bromo-2′- chloro-5′-methoxybiphenyl-2-amine (0.993 g, 47 %) as a white solid; 1H NMR (400 MHz, CDCI3) delta 3.73 (3H, s), 3.95 (2H, s), 6.61 (1 H, t), 6.73 – 6.78 (1 H, m), 6.83 (1 H, d), 6.92 – 6.94 (1 H, m), 7.31 – 7.34 (1 H, m), 7.38 – 7.40 (1 H, m)

The synthetic route of 608-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KUDOS PHARMACEUTICALS LIMITED; CANCER RESEARCH TECHNOLOGY LIMITED; FRIGERIO Mark; HUMMERSONE, Marc, Geoffrey; MENEAR, Keith, Allan; FINLAY, Maurice, Raymond, Verschoyle; GRIFFEN, Edward, Jolyon; RUSTON, Linette, Lys; MORRIS, Jeffrey, James; TING, Attila, Kuan, Tsuei; GOLDING, Bernard, Thomas; GRIFFIN, Roger, John; HARDCASTLE, Ian, Robert; RODRIGUEZ-ARISTEGUI, Sonsoles; WO2010/136778; (2010); A1;,
Bromide – Wikipedia,
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Electric Literature of 61613-22-7, The chemical industry reduces the impact on the environment during synthesis 61613-22-7, name is 2-Bromo-N-phenylaniline, I believe this compound will play a more active role in future production and life.

Di-tert-butyl dicarbonate (BOC) at room temperature in a 500 ml single-necked flask(0.2 mol, 43.6 g) was added to 400 ml of tetrahydrofuran.Then add N-(dibromophenyl)aniline (0.1 mol, 24.8 g),Pass N2 for 20 minutes and addHeat to reflux and stir24 hours. Then pour the mixture into 1L of water.The product was extracted with dichloromethane.The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed after separation.Separation and purification by silica gel column to obtain colorless oily liquid(33.0 g, yield 95%).

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-N-phenylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenzhen Huaxing Optoelectric Co., Ltd.; Wu Yuanjun; Jiao Shibo; Shi Ting; Su Shijian; Li Wei; Li Binbin; (20 pag.)CN109438350; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 58971-11-2, 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. 58971-11-2, name is 3-Bromophenethylamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 7-(2-Bromoethyl)-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione (4) (100 mg, 0.32 mmol) was dissolved in dryCH2Cl2 (30 mL) and cooled to 0 C. A solution of PBr3 (90 lL,0.94 mmol) in dry CH2Cl2 (20 mL) was added dropwise. The solutionwas allowed to warm to rt and stirred for 1 h. Then it was cooled to0 C again and the excess of PBr3 was carefully hydrolyzed by slowaddition of saturated aq NaHCO3 solution (5 mL). The pH was set at8 by addition of more saturated aq NaHCO3 solution. Then, theorganic layer was separated and the aqueous layer extracted withCH2Cl2 (2 50 mL). The combined organic extracts were dried overNa2SO4 and the solvent was removed under reduced pressure. Thecrude 7-(2-bromoethyl)-8-bromo-1,3-dimethylpurine-2,4-dione (5) was dissolved in a mixture of dimethoxyethane (10 mL) anddiisopropylethylamine (DIPEA) (0.5 mL). Then, the appropriateamine (0.64 mmol)wasadded and the solutionwasstirred overnightat rt. The volatiles were removed under reduced pressure andtetrahydropyrazino[2,1-f]purinediones 6-63 precipitated uponaddition ofH2O(20 mL). For purification, thecompounds were eitherfiltered off and washed with H2O (3 5 mL) and subsequently withdiethylether (3 10 mL), or subjected to column chromatography(silica gel, gradient of CH2Cl2/MeOH 1:0 to 40:1).

The chemical industry reduces the impact on the environment during synthesis 3-Bromophenethylamine. I believe this compound will play a more active role in future production and life.

Reference:
Article; Brunschweiger, Andreas; Koch, Pierre; Schlenk, Miriam; Rafehi, Muhammad; Radjainia, Hamid; Kueppers, Petra; Hinz, Sonja; Pineda, Felipe; Wiese, Michael; Hockemeyer, Joerg; Heer, Jag; Denonne, Frederic; Mueller, Christa E.; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5462 – 5480;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, molecular formula is C15H23Br, 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: 21524-34-5

A 20 mL oven-dried Schlenk tube was charged with magnesium (57.6 mg, 2.4 mmol) and anhydrous THF (1.5 mL), 5 drops of diisobutylaluminium hydride (DIBAL) was added and stirred for 5 min to activate magnesium. 2-bromo-1,3,5-triisopropylbenzene (566 mg, 2 mmol) was added potion-by-potion with vigorous stirring. The tube was capped with a rubber septum and was heated to 70 C. for 2 h. 1-bromo-2-iodo-3,4-dimethoxybenzene (700 mg, 2.1 mmol) in anhydrous THF (3 mL) was injected through syringe. An additional 1 mL of THF was used to rinse the reaction and was also transferred into the mixture. The combined reaction mixture was stirred at 70 C. overnight. At this time, the mixture was cooled to 0 C. using ice bath, and iodine (1.3 g, 5 mmol) in 6 mL anhydrous THF was added drop-wise over 10 min, then the reaction mixture was stirred for 30 min, and then warmed to stir at room temperature for 2 h. Then, the mixture was quenched with saturated Na2S2O3 (aq.) solution until the red color of bromine disappeared. The aqueous phase was extracted with Et2O (20 mL¡Á3) and the combined organic phases were dried over anhydrous MgSO4. After concentration, the crude product was purified by silica gel chromatography (EtOAc/petroleum ether=1/20) followed by crystallization in methanol to get a white solid (415 mg, 40%), labeled as 23MeOTIP-I. 1H NMR (600 MHz, Chloroform-d) delta 7.41-7.31 (m, 4H), 7.27-7.23 (m, 1H), 7.20 (s, 1H), 7.00 (d, J=8.3 Hz, 1H), 6.94 (d, J=8.3 Hz, 1H), 3.94 (s, 3H), 3.90 (s, 3H), 2.76-2.66 (m, 1H), 2.51 (p, J=6.9 Hz, 1H), 2.38 (p, J=6.9 Hz, 1H), 1.26 (d, J=6.9 Hz, 3H), 1.13 (d, J=6.9 Hz, 6H), 1.08 (d, J=6.9 Hz, 3H), 1.04 (d, J=6.8 Hz, 3H), 0.80 (d, J=7.3 Hz, 3H), 0.76 (d, J=7.2 Hz, 3H) ppm. 13C NMR (151 MHz, CDCl3) delta 150.79, 148.74, 144.81, 143.30, 142.70, 142.16, 137.90, 131.47, 130.65, 127.18, 126.35, 126.27, 119.60, 119.38, 111.62, 60.37, 55.93, 32.28, 31.97, 30.58 (d), 29.79 (d), 25.09, 24.98, 24.32 (t), 23.58, 23.45 ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 21524-34-5, its application will become more common.

Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 101417-40-7, 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. 101417-40-7, name is 4-(Bromomethyl)benzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

a 1,3-Benzodioxole-4-methanethiol The subtitled compound (0.29 g) was prepared by the method of Example 6, step (c) using 4-(bromomethyl)-1,3-benzodioxole (0.51 g). MS (EI) 168 (M+), 135 (100%).

The synthetic route of 4-(Bromomethyl)benzo[d][1,3]dioxole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bonnert, Roger; Gardiner, Stewart; Hunt, Fraser; Walters, Iain; US2003/55250; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 112279-72-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 112279-72-8 name is 4-Bromo-2,3-difluoroaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

N-((4-bromo-2,3-difluorophenyl)carbamothioyl)benzamide was prepared according to the following procedure. To 4-bromo-2,3-difluoroaniline (3.70 g, 17.8 mmol) dissolved in acetone (20 mL) was added benzoyl isothiocyanate (2.90 g, 2.39 mL, 1 eq, 17.8 mmol) drop-wise. The reaction was stirred for 30 min at 18 C, the mixture was filtered, the collected white solid was washed with heptane (50 mL) and vacuum dried to afford N-((4-bromo-2,3-difluorophenyl)carbamothioyl)benzamide (5.68 g, 85%) as a white solid.?H NMR (300 MHz, DMSO-ifc) d 12.45 (s, 1H), 11.91 (s, 1H), 8.46 – 7.88 (m, 2H), 7.78 – 7.26 (m, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,3-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; ACUCELA INC.; ORME, Mark, W.; ZUNIGA, Edison, S.; KUKSA, Vladimir, A.; CRAFT, Russell, Stuart; SAVEEDRA, Eduardo, Moreno; MEISSNER, Johannes, Wilhelm, Georg; DEN HARTOG, Jacobus, Antonius, Joseph; DROS, Albert, Cornelis; (223 pag.)WO2020/69330; (2020); A2;,
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. 7499-66-3, name is 6-Bromonaphthalen-2-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 6-Bromonaphthalen-2-amine

Example 15 Synthesis of 2-bromo-6-(N-methylamino)Naphthalene (Intermediate 27) A solution of 2-amino-6-bromonaphthalene (2.0 g) in 1,4-dioxane (30 ml) was added dropwise with dimethyl sulfate (1300 mul) and stirred at room temperature for 46 hours.The reaction mixture was added with ethyl acetate (90 ml) and then added with 1 N aqueous sodium hydroxide (5 ml).This mixture was extracted with ethyl acetate (150 ml*3).The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure.The residue was purified by flash column chromatography (hexane:ethyl acetate=15:1) to obtain the title compound (Intermediate 27, 152 mg).

The synthetic route of 7499-66-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shoda, Motoshi; Kuriyama, Hiroshi; US2004/44258; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 3-L round bottom flask equipped with a mechanical stirrer, a heating mantle, a thermal couple, a reflux condenser, a nitrogen inlet and a nitrogen outlet was charged with 7- bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (Compound 11, 100 g, 469 mmol) and tert- butyl 4-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine- 1 (2T/)-carboxylate (Compound 12, 174 g, 563 mmol) in l,4-dioxane (876 mL) at room temperature. To the reaction flask was added potassium carbonate (130 g, 939 mmol) and water (218 g) in sequence. The mixture was degassed by exposure to vacuum and refilled with nitrogen atmosphere for three times. After the addition of tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4, 13.56 g, 11.7 mmol), the reaction mixture was degassed and refilled with nitrogen for three times at room temperature. Then the reaction mixture was heated to 85 – 90 C, and agitated at that temperature for 16 hours. Upon the completion of the reaction, water (900 mL) was added in 30 minutes while the internal temperature was above 50 C. The mixture was cooled to room temperature. Solids gradually precipitated out. The solids were collected by filtration at 18 C, and washed with water (2 x 250 mL) and methyl /eN-butyl ether (MTBE, 3 x 200 mL). The wet cake was put back into the reaction flask, and agitated in MTBE (750 mL) at 50 C for 1 hour. The solids were collected at room temperature by filtration. The cake was dried in a vacuum oven at 50 C under vacuum with nitrogen sweeping for 72 hours to provide tert-butyl 4-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)-5,6- dihydropyridine- 1 (2H)-carboxylate (Compound 13, 123.7 g, 84%) as a brown solid. ‘H NMR (500 MHz, DMSO-i) d 7.89 (s, 1H), 7.69 (s, 2H), 7.00 (s, 1H), 6.91 (d, J= 4.6 Hz, 1H), 6.69 (d, J= 4.5 Hz, 1H), 4.06 (s, 2H), 3.55 (t, J= 5.5 Hz, 2H), 2.59 – 2.52 (m, 2H), 1.43 (s, 9H) ppm; C16H21N5O2 (MW 315.37), LCMS (El) m/e 316.1 (M+ + H).

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, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; INCYTE CORPORATION; ROCCO, William L.; MULLER, Francis X.; (0 pag.)WO2020/6408; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary