Tag: M.W=200-300

40161-54-4, Adding some certain compound to certain chemical reactions, such as: 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, 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 40161-54-4.

Example 42: N-(5-Fluorothiazol-2-yl)-5-(2-(4-methylpiperazin-l-yl)-4- (trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(lH)-sulfonamide Step 1 : 5-(2-(4-Methyl-lH-imidazol-l-yl)-4-(trifluoromethyl)phenyl)isoquinoline A suspension of sodium hydride 60% (0.330 g, 13.75 mmol) in 8 mL DMF was cooled to 0 C and was treated with 4-methyl-lH-imidazole (0.676 g, 8.23 mmol). After stirring for 40 minutes, l-bromo-2-fluoro-4-(trifluoromethyl)benzene (1.180 ml, 8.23 mmol) was added, and the reaction mixture was heated to 120 C for 90 minutes. At this point Cl2Pd(AmPhos) (Sigma-Aldrich, St. Louis, MO, 0.291 g, 0.412 mmol), isoquinolin-5- ylboronic acid (1.424 g, 8.23 mmol), potassium phosphate (6.99 g, 32.9 mmol), 16 mL dioxane and 12 mL water were added, and the reaction mixture was heated to 120 C overnight. The reaction mixture was poured into saturated aHC03 solution and was extracted with DCM. The organics were concentrated then purified by reverse phase column chromatography [RediSep Gold C18 150g, 15 to 100% (0.1% NH40H in MeOH)/(0.1% NH40H in water)] yielding 5-(2-(4-methyl-lH-imidazol-l-yl)-4- (trifluoromethyl)phenyl)isoquinoline (1.435 g, 4.06 mmol) as an about 4: 1 mixture of isomers.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 40161-54-4.

Reference:
Patent; AMGEN INC.; DINEEN, Thomas; KREIMAN, Charles; WEISS, Matthew; GEUNS-MEYER, Stephanie; WO2013/134518; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

937046-98-5, 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. 937046-98-5 name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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.

To a solution of [3-(4,4,5,5-tetramethyl-[1,3,2]ciioxaborolan-2-yl)-benzyl]-carbamic acid tert-butyl ester (7 g, 21 mmol) in DME (100 mL), 7-bromo-pyrro]o[2,1-f][1 ,2,4]triazin-4- ylamine (2.5 g, 11.7 mmol), PdCI2(dppf) complexed with CH2CI2 (850 mg, 1.2 mmol) and 2 N Na2CO3 (12 mL) were added. The mixture was degassed for 20 min and was then heated to 80 0C for 23 hours. After cooling, the mixture was partitioned between EtOAc and H2O, and the organic layer was separated and dried. Biotage chromatography (50- 100% EtOAc) provided the title product as off white solid 2.6 g (76%). 1H NMR (300 MHz, DMSO-cfe) 57.80-7.50 (m, 6 H), 7.20-7.0 (m, 3 H), 4.80 (s, 2 H), 1.30 (s, 9 H); ES- MS m/z 339 [M+H]+, HPLC RT (min) 2.41.

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; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

24358-62-1,Some common heterocyclic compound, 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, molecular formula is C8H10BrN, 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 solution of 4-bromo-a-methylbenzylamine (6.57 mmol) and N,N-diisopropylethylamine (9.85 mmol) in anhydous THF (30 mL) and 2-methoxybenzoyl chloride (7.22 mmol) at 0 C was then allowed to return to RT and stirred for 15 h. The mixture was quenched with a saturated solution of ammonimum chloride (40 mL), extracted with EtOAc (3×20 mL). The combined organic extracts were washed with water (2×30 mL), a saturated solution of brine (30 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. Further purification gave the titled compound (6.19 mmol) as a white solid. UPLC-MS (ES, Short acidic): 1 .96 mi m/z 336.1 [M+2]

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(4-Bromophenyl)ethylamine, its application will become more common.

Reference:
Patent; REDX PHARMA PLC; GUISOT, Nicolas; (266 pag.)WO2017/103611; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

68322-84-9, Adding a certain compound to certain chemical reactions, such as: 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, 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 68322-84-9.

EXAMPLE 4 4-Trifluoromethyl-10-aza-tricyclo[6.3.1.02,7]-dodeca-2(7),3,5-triene Hydrochloride (See Grunewald, G. L.; Paradkar, V. M.; Pazhenchevsky, B.; Pleiss, M. A.; Sall, D. J.; Seibel, W. L.; Reitz, T. J. J. Org. Chem. 1983, 48, 2321-2327. Grunewald, G. L.; Markovich, K. M.; Sall, D. J. J. Med. Chem. 1987, 30, 2191-2208.) The title compound was prepared by the methods described in Examples 1 and 2 starting with 2-fluoro-5-trifluoromethylbromobenzene. 1H NMR (400 MHz, CD3OD) delta 7.71 (s, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 3.46 (m, 4H), 3.21 (d, J=12.5 Hz, 2H), 2.41 (m, 1H), 2.16 (d, J=11.5 Hz, 1H). APCI MS m/e 228.2 [(M+1)+]. (HCl salt) M.p. 244-246 C. Anal. Calcd. for C12H12F3N.HCl.1/3H2O: C, 53.44; H, 5.11; N, 5.19. Found C, 53.77; H, 4.82; N, 5.18.

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-1-fluoro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pfizer Inc; US6605610; (2003); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

6138-90-5, 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. 6138-90-5, name is Geranyl bromide belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 26 (4E)-2-(4Methoxy-benzenesulfonyl)-5,9-dimethyl-2-[4-(2-morpholin-4-yl-ethoxy) -benzyl]-deca-4,8-dienoic acid hydroxyamide To a stirred solution of (4-methoxy-benzenesulfonyl)-acetic acid ethyl ester (5.16 g, 20 mmol), geranyl bromide (4.2g, 20 mmol) and 18-Crown-6 (500 mg) in acetone (250 ml) was added K2CO3 (10 gms, excess) and the mixture refluxed foe 24 hours. At the end, the reaction mixture was filtered and the acetone layer was concentrated. The residue obtained was extracted with chloroform, washed well with water, dried over anhydrous MgSO4, filtered and concentrated. The product obtained was purified by silica-gel column chromatography, eluding with 30% ethy acetate: hexane. The product 2-(4-methoxy-benzenesulfonyl)-5,9-dimethyl-deca-4,8-dienoic acid ethyl ester was isolated as a colourless oil. Yield: 7.0 g, 89%.

The synthetic route of Geranyl bromide has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6172057; (2001); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1559-88-2, name is 3-Bromo-1,2,4,5-tetrafluorobenzene, 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. 1559-88-2

General procedure: An oven-dried Schlenk tube equipped with a stir bar was charged with Pd(OAc)2 (4.5 mg, 0.02 mmol, 10 mol%), aryliodine(III) diacetate (0.24 mmol) and Ag2CO3 (82.7 mg, 0.3 mmol). The tube was fitted with a rubber septum, and then it was evacuated and refilled with nitrogen three times. Under nitrogen, polyfluoroarene (0.2 mmol), DMSO(0.1 mL) and DMF (2 mL) were added successively. The rubber septum was replaced with a Teflon screw cap under nitrogen flow. With stirring, the reaction mixtures were heated at 110 C for the indicated amount of time (unless otherwise specified), and then cooled down to roomtemperature. The resultant mixture was filtered through a short plug of silica gel and then concentrated in vacuo. The residue was then purified by flash chromatography on silica gel to provide the corresponding product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1559-88-2.

Reference:
Article; Fu, Zhengjiang; Xiong, Qiheng; Zhang, Wenbiao; Li, Zhaojie; Cai, Hu; Tetrahedron Letters; vol. 56; 1; (2015); p. 123 – 126;,
Bromide – Wikipedia,
bromide – Wiktionary

4549-33-1, 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 4549-33-1 as follows.

4-Picoline (2.0 mL, 21 mmol) was dissolved in THF (40 mL) under an argon atmosphere using a 150 mL Schlenk flask. The Schlenk flask was cooled down to-78C by using a dry ice/methanol cooling bath. A solution of n-butyllithium in hexane (12.0 mL, 18 mmol) was added to the solution by a syringe under an argon atmosphere. After the solution was stirred for 30 min, diethyl amine (2.2 mL, 22 mmol) was added to the solution by a syringe under an argon atmosphere. After the solution was stirred for 30 min, the solution was added to a solution of 1,9-dibromononane (20.0 mL, 99 mmol) in THF (10 mL) by a syringe under an argon atmosphere. The reaction mixture was gradually warmed to room temperature and stirred for 1 h. The solution was poured into 0.5M ammonium chloride (10 0mL) to quench the reaction at 0C. After evaporation of the organic solvent at 0C, the residual solution was dropped into 1M hydrobromic acid (100 mL), and the product was extracted with dichloromethane (4¡Á50 mL). The organic layers were combined, and dried with sodium sulfate (15 g). The organic layer was concentrated under reduced pressure. After the residual solution was dropped into hexane (200 mL), and then a pale yellow precipitate was formed. The pale yellow precipitate containing the product was recovered by centrifugation. The product 1 was obtained as a pale yellow powder (yield 5.12g, 65%). 1H NMR (500MHz, DMSO-d6): delta 8.42 (d, J=5.9Hz, 2H), 7.19 (d, J=5.9Hz, 2H), 3.50 (t, J=6.7Hz, 2H), 2.57 (t, J=7.6Hz, 2H), 1.81-1.72 (m, 2H), 1.61-1.52 (m, 2H), 1.39-1.20 (m, 12H).

According to the analysis of related databases, 1,9-Dibromononane, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hashidzume, Akihito; Kuse, Akihiro; Oshikiri, Tomoya; Adachi, Seiji; Yamaguchi, Hiroyasu; Harada, Akira; Tetrahedron; vol. 73; 33; (2017); p. 4988 – 4993;,
Bromide – Wikipedia,
bromide – Wiktionary

1435-51-4, 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. 1435-51-4 name is 1,3-Dibromo-5-fluorobenzene, 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.

Sodium methoxide (8.80 ml of a 4.5M solution in methanol, 39.6 mmol) was added dropwise to a stirred solution of 3,5-dibromofluorobenzene (5.00 g, 19.0 mmol) in N,N-dimethylformamide (95 ml) at 0 C. under nitrogen. The reaction was allowed to warm to room temperature, stirred for 1 hour and then concentrated under reduced pressure. The residue was dissolved in ether (500 ml) and the resulting solution was washed with water (3¡Á300 ml) and brine (300 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to provide the title compound (5.13 g) as a white solid. 1H-NMR (300 MHz, CDCl3): delta=3.79 (s, 3H), 7.00 (s, 2H), 7.26 (s, 1H). LRMS (thermospray): m/z [MH+] 266. Microanalysis: Found: C, 31.56; H, 2.29. C7H6OBr2 requires C, 31.62; H, 2.27%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US2005/54707; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

49764-63-8,Some common heterocyclic compound, 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, molecular formula is C6H6Br2N2, 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.

General procedure: A solution of intermediate 6 (1.0 equiv.) and substituted o-phenylenediamine (1.0 equiv.) in 15 mL acetonitrile was stirred at roomtemperature overnight. TLC was used to monitor the progress of the reaction. When the reaction finished, the mixture was addedBOP (1.5 equiv.) and DBU (2.0 equiv.) and was stirred at room temperature. TLC was used to monitor the progressof the reaction. The solutionwas treated with water and ethyl acetate. The organic phases were combined anddried over and evaporated to dryness under reduced pressure. Purification bychromatography using petroleum ether/ethyl acetate 2:1 yielded 7a.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 49764-63-8, its application will become more common.

Reference:
Article; Bu, Huagang; Jia, Lejiao; Li, Jun; Li, Zhenyu; Li, Zhiying; Shen, Chengwu; Tang, Hui; Wu, Xingkang; Zhang, Rui; Bioorganic and medicinal chemistry letters; (2020);,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, 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 327-52-6. 327-52-6

To magnesium spalls in a reaction flask, under an atmosphere of nitrogen, was added 50 ml tetrahydrofuran and 0.02 g iodine as an initiator. A solution of 9 g 1-bromo-2,4,5-trifluorobenzene in 150 ml tetrahydrofuran was added dropwise into the reaction system. The reaction was stirred at 25 C. for 3 h to obtain a solution of 0.21 mol/L (2,4,5-trifluorophenyl)-magnesium bromide.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Bromo-2,4,5-trifluorobenzene.

Reference:
Patent; ZHEJIANG JIUZHOU PHARMACEAUTICAL CO., LTD.; Gao, Hongjun; Li, Min; US2013/12735; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary