Tag: M.W=100-200

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. 10269-01-9, name is (3-Bromophenyl)methanamine, A new synthetic method of this compound is introduced below., name: (3-Bromophenyl)methanamine

To a stirred solution of 2-methyl-1-(4- methylsulfonyl-5,6,7,8- tetrahydroquinazolin-2-yl)indole-4-carbonitrile (400 mg, 1.09 mmol) in MeCN (50 ml) were added (3-bromophenyl)methanamine (2 g, 10.92 mmol) and TEA (1g, 10.92 mmol). The reaction mixture was refluxed for 2 days, then concentrated in vacuum and purified by column chromatography on silica gel column (hexane/ethyl acetate) to afford 1-[4-[(3- bromophenyl)methylamino]-5,6,7,8-tetrahydroquinazolin-2-yl]-2-methyl-indole- 4-carbonitrile (0.5 g, 87.3%) as a brown solid. LCMS (M+H+) m/z: Calcd:

The synthetic route of 10269-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CLEAVE BIOSCIENCES, INC.; ZHOU, Han-Jie; WUSTROW, David; (498 pag.)WO2016/200840; (2016); A1;,
Bromide – Wikipedia,
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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 2550-36-9 as follows. Safety of (Bromomethyl)cyclohexane

179a) (3-Bromophenyl)(cyclohexylmethyl)sulfane To a solution of 3-bromobenzenethiol (4.158 g, 21 .99 mmol) in DMF (30 ml_) was added K2C03 (9.12 g, 66.0 mmol). The reaction mixture was stirred for 30 mins at room temperature. Then (bromomethyl)cyclohexane (4.28 g, 24.19 mmol) was added. The reaction mixture was stirred at 25C for 16 h. Then it was poured into water (50ml_) and extracted with ethyl acetate(3x). The combined organic phase was concentrated to obtain the title compound (3-bromophenyl)(cyclohexylmethyl)sulfane (6g, 18.93 mmol, 86 % yield) which was used in the next step without further purification.

According to the analysis of related databases, 2550-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; CALLAHAN, James Francis; KERNS, Jeffrey K.; LI, Peng; LI, Tindy; MCCLELAND, Brent W.; NIE, Hong; PERO, Joseph E.; DAVIES, Thomas Glanmor; GRAZIA CARR, Maria; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; NORTON, David; VERDONK, Marinus Leendert; WOOLFORD, Alison Jo-Anne; WILLEMS, Hendrika Maria Gerarda; (664 pag.)WO2017/60854; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1422-53-3, 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. 1422-53-3, name is 2-Bromo-4-fluorotoluene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 7 2-Bromo-4-fluoro-benzaldehyde diethyl acetal To a solution of 6.5 g of 2-bromo-4-fluoro-benzaldehyde (prepared by the oxidation of 2-bromo-4-fluoro-toluene by the method reported by V. J. Bauer, B. J. Duffy, D. Hoffman, S. S. Klioze, R. W. Kosley, Jr., A. R. McFadden, L. L. Martin, H. H. Ong and H. M. Geyer III, J. Med. Chem., 1976, 19, 1315) in 25 ml of ethanol was added triethylorthoformate followed by 0.05 g of p-toluene sulfonic acid. The solution was stirred at room temperature for 2.25 h then diluted with 100 ml of a 5% sodium carbonate solution and extracted with two 100 ml portions of ether. The combined organic layers were washed with 50 ml of brine and dried over sodium sulfate. Evaporation of the solvent yielded 8.8 g of 2-bromo-4-fluoro-benzaldehyde diethyl acetal as an oil, 1 H NMR (200 MHz; CDCl3)deltaH 5.60 (CHO3).

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-4-fluorotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Akzo Nobel, N.V.; US6080773; (2000); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 51376-06-8,Some common heterocyclic compound, 51376-06-8, name is 5-Bromobenzo[c][1,2,5]oxadiazole, molecular formula is C6H3BrN2O, 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.

6-(Methylsulfonyl)-4-quinolinamine (50 mg, 0.225 mmol), 5-bromo-2,1,3-benzoxadiazole, Pd2dba3 (20.60 mg, 0.022 mmol), BINAP (14.01 mg, 0.022 mmol), and sodium tert-butoxide (43.2 mg, 0.450 mmol) were added to a vial which was purged with nitrogen. Toluene (2250 mul) was then added and the reactions were heated to 120 C for 20 min via microwave. It was then concentrated, redissolved in DMSO, filtered, and purified by RP HPLC to afford the title compound as a solid (11 mg, 14 %). 1H NMR (400 MHz, DMSO-d6) delta 9.26 (s, 1H), 8.82 (d, J = 5.1 Hz, 1H), 8.39 (d, J = 8.5 Hz, 1H), 8.23 (m, 2H), 7.95 (br. s, 1H), 7.72 (d, J = 9.5 Hz, 1H), 7.40 – 7.46 (m, 1H), 3.38 (s, 3H); MS (m/z) 341.1 (M+H+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromobenzo[c][1,2,5]oxadiazole, its application will become more common.

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

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. 4333-56-6, name is Bromocyclopropane, A new synthetic method of this compound is introduced below., Formula: C3H5Br

10 mg of Compound 9 was weighed into 5 mL of THF, 5 mg of NaH was added, and the mixture was stirred at room temperature for half an hour. Twenty-fiveBromide cyclopropane, 50 C reaction 6h, TLC detection reaction material almost completely disappeared, adding saturated ammonium chloride to stop the reactionAfter extraction with ethyl acetate twice, the organic layer was dried over anhydrous sodium sulfate, concentrated, and purified by silica gel column chromatography (eluent EtOAc /Petroleum ether = 20: 1 to 10: 1) to give Compound 11 (9.5 mg) in 85% yield, ESI-MS m / z: 409.2 [M + Na]Ie ^: detection purity of 96.6%.

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; Yangzhou University; Chen Min; Yu Yue; (16 pag.)CN104710396; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 7051-34-5, name is (Bromomethyl)cyclopropane, A new synthetic method of this compound is introduced below., Safety of (Bromomethyl)cyclopropane

L-Cysteine (100 g, 0.825 mol) was suspended in ethanol (850 mL). A solution of sodium hydroxide (1.65 mol) in ethanol (650 mL) was added during 40 min at 20-25 C. To the solution was added bromomethylcyclopropane (0.907 mol) at 25-30 C. The reaction mixture was stirred at ambient temperature overnight, the neutralized with 2N HCl (300 mL). The suspension was concentrated under vacuum to 400 mL, then water (750 mL) was added, and pH was adjusted to 6.5 with 2N HCl. The mixture was stirred for 2 h at 0-5 C., the precipitate was filtered, washed with water and dried under vacuum to give (R)-2-amino-3-cyclopropyl-methylsulfanylpropionic acid as a white crystalline solid (128.2 g; yield=88.6 %). C7H13NO2S; MW=175.3; Tmelt=2090 C; NMR (DMSO, ppm): 0.20 (m, 2H), 0.50 (m, 2H), 0.94 (m, 1H), 2.50 (m, 2H), 2.78 (dd, J=14.5 and 8.5 Hz, 1 H), 3.08 (dd, J=14.5 and 4 Hz, 1 H) and 7.64 (ls, 1H (mobile)); SM (EI; m/z): 130 (M+-COOH), 89, 74.

The synthetic route of 7051-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AXYS PHARMACEUTICALS, INC.; AVENTIS PHARMACEUTICALS, INC.; US2004/19218; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 7745-91-7, 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. 7745-91-7 name is 3-Bromo-4-methylaniline, 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.

Method 8; JV-(3-Bromo-4-methylphenylV3-(trifluoromethyl>)benzaniide3-(Trifluoromethyl)benzoyl chloride (0.78 ml, 5.2 mmol) was added to a stirring solution of 3-bromo-4-methylaniline (0.74 g, 4.0 mmol) and triethylamine (1.65 ml, 12 mmol) in 15 ml DCM. The mixture was stirred at 25 0C for 4 h. The reaction mixture was washed with 1 N HCl, 10 % NaOH, water and brine. The combined organics were dried and concentrated under reduced pressure. The resulting residue was used without further purification; m/z 359

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

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/79791; (2006); 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. 2550-36-9, name is (Bromomethyl)cyclohexane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H13Br

[0307] A four-necked reactor equipped with a thermometer was charged with 3.00 g (18.2 mmol) of 2-hydrazinobenzothiazole and 30 ml of DMF under a nitrogen stream to prepare a homogeneous solution. After the addition of 7.55 g (54.6 mmol) of potassium carbonate and 3.86 g (21.8 mmol) of (bromomethyl)cyclohexane to the solution, the mixture was stirred at 80C for 9 hours. After completion of the reaction, the reaction mixture was cooled to 20C, added to 300 ml of water, and extracted with 500 ml of ethyl acetate. After drying the ethyl acetate layer over anhydrous sodium sulfate, sodium sulfate was filtered off. Ethyl acetate was evaporated from the filtrate under reduced pressure using a rotary evaporator to obtain a yellow solid. The yellow solid was purified by silica gel column chromatography (n-hexane:ethyl acetate=85:15 (volume ratio)) to obtain 2.36 g of an intermediate S as a white solid (yield: 49.7%). [0308] The structure of the target product was identified by 1H-NMR. [0309] 1H-NMR (400 MHz, CDCl3, TMS, delta ppm): 7.58 (d, 1H, J=8.0 Hz), 7.51 (d, 1H, J=8.1 Hz), 7.26 (dd, 1H, J=7.0 Hz, 8.1 Hz), 7.04 (dd, 1H, J=7.0 Hz, 8.0 Hz), 4.24 (s, 2H), 3.59 (d, 2H, J=7.4 Hz), 1.84-1.92 (m, 1H), 1.67-1.77 (m, 5H), 1.16-1.29 (m, 3H), 1.02-1.13 (m, 2H).

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 2550-36-9.

Reference:
Patent; Zeon Corporation; SAKAMOTO Kei; OKUYAMA Kumi; EP2703385; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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: To a solution of 3-substituted-2-haloimidazo[4,5-b]pyridine derivative (1 equiv) in NMP, were added terminal acetylene (1.5 equiv) and tetrabutyl ammonium acetate (1.5 equiv). The solution was purged with nitrogen and stirred at room temperature for 0.15 h, at that time PdCl2(PCy3)2 was added. The reaction solution was purged again with nitrogen and then placed in the microwave and heated for 10 to 30 min at 110 C (for iodide and bromide intermediates). When chloro intermediate was used, the reaction contents were heated at 150 C. When TLC and LCMS showed full consumption of starting materials, the reaction mixture was diluted with ethyl acetate, separated the ethyl acetate layer, given water wash, brine wash and was dried over anhydrous sodium sulphate and concentrated to get the crude material. The crude product was directly purified by column chromatography (0-15% hexane/EtOAc) to isolate the 3-alkyl-2-akynyl imidao[4,5-b]pyridine derivatives.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromophenylacetylene, its application will become more common.

Reference:
Article; Sajith, Ayyiliath M.; Muralidharan; Tetrahedron Letters; vol. 53; 39; (2012); p. 5206 – 5210;,
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 766-81-4 as follows. Safety of 3-Bromophenylacetylene

In a 25 mL roundbottom flask, 1-bromo-3-ethynylbenzene (243 muL, 1.94 mmol, 1.1 equiv) was dissolved in 10 mL THF and cooled to-78 C. A solution of LiHMDS (1 M in THF, 1.9 mL, 1.85 mmol, 1.05 equiv) was added dropwise, then the mixture allow to warm to room temperature and stir for 15 min. The reaction was cooled again to-78 C and a solution of 3-((tert-butyldiphenylsilyl)oxy)propanal (552 mg, 1.77 mmol, 1.0 equiv) in 1.8 mL THF was added by cannula. The reaction was allowed to warm to room temperature and was stirred for 12 hr.10 mL saturated aqueous NH4Cl was added to quench the reaction, followed by 10 mL Et2O, then the aq layer was extracted with Et2O (3 × 10 mL). The combined organic extracts were washed with brine (1 × 10 mL), dried (MgSO4), filtered, and concentrated by rotary evaporation. Purification by silica flash chromatography (10-20% EtOAc/hexanes) yielded the propargyl alcohol as a clear yellow oil (802 mg, 92%). TLC: Rf 0.49 (20% EtOAc/hexanes). 1H-NMR (600 MHz): delta 7.76- 7.64 (m, 4H), 7.56 (t, J = 1.8 Hz, 1H), 7.48- 7.32 (m, 8H), 7.18 (t, J = 7.9 Hz, 1H), 4.92 (td, J = 6.4, 4.3 Hz, 1H), 4.12 (ddd, J = 10.5, 8.2, 3.7 Hz, 1H), 3.89 (ddd, J = 10.3, 5.9, 4.2 Hz, 1H), 3.49 (d, J = 6.4 Hz, 1H), 2.20- 2.07 (m, 1H), 2.03- 1.96 (m, 1H), 1.06 (s, 9H). 13C-NMR (151 MHz): delta 135.5, 134.5, 132.7, 131.5, 130.3, 129.9, 129.7, 127.8, 124.7, 122.0, 91.0, 83.5, 62.2, 61.9, 38.5, 26.8, 19.0.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE BROAD INSTITUTE, INC.; UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.; MCKERROW, James; DANDAPANI, Sivaraman; EDWANKAR, Rahul; TAN, Derek, Shieh; FOLEY, Corinne, N.; MOURA-LETTS, Gustavo; VERANO, Alyssa; CHAKRABARTI, Debopam; ROBERTS, Bracken; (258 pag.)WO2017/124087; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary