Category: chlorides-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 129482-45-7, name is 4-Benzyl-2-(chloromethyl)homomorpholine, belongs to chlorides-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 129482-45-7, name: 4-Benzyl-2-(chloromethyl)homomorpholine

EXAMPLE 54 (4-Benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80 Aniline (2.59 mL, 28.4 mmol) and NaI (4.06 g, 27.1 mmol) were added to a solution of 4-benzyl-2-chloromethyl-1,4-oxazepane (79) (6.49 g, 27.1 mmol) in n-butanol (68 mL, 0.4 M), and the reaction was heated to 110 C. until the reaction was judged complete by TLC (4 h). The reaction was cooled to room temperature, and water and CH2Cl2 were added. The organic layer was removed, and the aqueous layer was extracted with CH2Cl2 (2*). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to achieve (4-benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80, which was used without purification in the next reaction. 1H NMR (partial, CDCl3) 4.08-3.86 (3H, m), 3.80 (1H, d, J=13.3 Hz), 3.73 (1H, d, J =13.3 Hz), 3.22-3.05 (2H,.m), 2.95-2.70 (3H, m), 2.64 (1H, dd, J=13.6, 7.6 Hz), 2.1-1.9 (2H, m) ppm. 13C NMR (CDCl3) 148.33, 139.38, 129.28, 129.11, 128.46, 127.23, 117.44, 113.13, 76.70, 67.49, 62.92, 59.35, 54.76, 46.93, 30.75 ppm. LRMS: 296.68.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Cuny, Gregory D.; Shao, Liming; Hauske, James R.; Heffernan, Michele L.R.; Aquila, Brian M.; Wu, Xinhe; Wang, Fengjiang; Bannister, Thomas D.; US2002/16337; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 59772-49-5 as follows. HPLC of Formula: C6H5BrClN

Benzofuran-3-ylboronic acid2-bromo-6-chloroaniline (189 g, 1100 mmol) was dissolved in toluene (Toluene), EtOH, H2O (400 mg, 400 mL). Pd (PPh3) 4 (58 g, 50 mmol) and NaHCO3 (252 g, 3000 mmol) were added thereto and refluxed for 4 hours. After completion of reaction, MC is extracted by cooling to room temperature. After drying over anhydrous MgSO4, the solvent is removed by rotary evaporator. Column chromatography (MC: Hx = 1: 3) was used to obtain the desired compound 461-5. (190 g, 91percent, brown oil)

According to the analysis of related databases, 59772-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; L Ti Material Co., Ltd.; Oh Han-guk; Lee Yun-ji; Ji Hye-su; Jeong Won-jang; Choi Jin-seok; Choi Dae-hyeok; (212 pag.)KR2019/33885; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 54773-20-5, A common heterocyclic compound, 54773-20-5, name is 1,3-Dichloro-5-(trifluoromethyl)benzene, molecular formula is C7H3Cl2F3, 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.

STEP A: 2,6-dichloro-4-(trifluoromethyl)benzaldehyde A 2M n-BuLi solution (5.8 mL, 11.6 mmol) was added to a -78 C. THF solution (60 mL) of 1,3-dichloro-5-(trifluoromethyl)benzene (2.5 g, 11.6 mmol). After 45 min neat DMF (0.39 mL, 5.0 mmol) was added, and the resulting solution was allowed to warm to 0 C. gradually, quenched with NH4Cl solution, and extracted with diethyl ether. The combined extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

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; Chakravarty, Devraj; Greco, Michael; Shook, Brian; Xu, Guozhang; Zhang, Rui; US2012/302641; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, belongs to chlorides-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 179897-90-6, Safety of 1,3-Dibromo-2-chloro-5-fluorobenzene

l,3-Dibromo-2-chloro-5-fluorobenzene (400 mg, 1.39 mmol) dissolved in toluene (4 mL) and 2- methyltetrahydrofuran (1 mL) was treated with the triisopropyl borate (390 pL, 1.69 mmol). The mixture was cooled to -78 C in a dry ice/acetone bath and then n-butyllithium (2.5 M in hexanes, 680 pL, 1.70 mmol) was added slowly dropwise. The mixture was maintained at -78 C for 1 h and then slowly allowed to warm to room temperature. After stirring for 1 h, the reaction mixture was quenched by adding 1N HC1 solution, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and purified by ISCO silica gel chromatography to give (3-bromo-2-chloro-5-fluorophenyl)boronic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 69411-05-8, These common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, 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 13 1-(5-Chloro-3-trifluormethyl-anilino)-4-(4-pyridyl-methyl)-phthalazine A suspension of 27.9 g (109 mMol) of 1-chloro-4-(4-pyridyl-methyl)-phthalazine (Example 67A.1 in WO 98/35958) and 21.4 g (109 mMol) of 5-amino-3-chloro-benzotrifluoride (Example 5b) in 500 ml of ethanol and 27.4 ml of 4 N HCl/dioxane is stirred during 3 h a 80 C. After cooling down, the reaction mixture is diluted with 0.3 l of ether, filtrated, and washed with ether. The remaining solid is then taken up in water and EtOAc, brought to alkaline pH by means of NH3 solution, stirred for 15 min at room temperature and then filtered and washed with ether (?raw product). The water layer is removed from the filtrate and extracted twice with ethyl acetate. The organic layers are washed with water and brine, dried over Na2SO4 and evaporated. The residue is combined with the raw product mentioned above, and the solid is dissolved in ethyl acetate and methanol. About 100 g SiO2 are added, followed by evaporation, and the powder is applied onto a silica gel column and eluted with ethyl acetate and subsequently with a mixture of ethyl acetate and methanol (98:2?95:5, v/v). Solving the obtained fractions in ethyl acetate/methanol, partial evaporation and crystallization by addition of ether/hexane leads to the title compound: m.p. 231-232 C.; An. calc. (C21H14N4ClF3) C, 60.81%; H, 3.40%; N, 13.51%; Cl, 8.55%; F, 13.74%; An meas. C, 60.8%; H, 3.4%; N, 13.5%; Cl, 8.5%; F, 13.8%; 1H-NMR (DMSO-d6) 9.63 (s, HN), 8.60 (d, 1H), 8.56 (s, 1H), 8.44 (d, 2H), 8.39 (s, 1H), 8.16 (d, 1H), 8.03 (t, 1H), 7.97 (t, 1H), 7.43 (s, 1H), 7.32 (d, 2H), 4.63 (s, 2H); FAB-MS (M+H)+=415.

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bold, Guido; Dawson King, Janet; Frei, Jorg; Heng, Richard; Manley, Paul William; Wietfeld, Bernhard; Wood, Jeanette Marjorie; US2003/13718; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1009102-44-6, These common heterocyclic compound, 1009102-44-6, name is 1-(4-Chlorophenyl)cyclopropanamine hydrochloride, 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.

In step 1 Manufactured 1-(4-chlorophenyl)cyclopropan-1-amine hydrochloride (0.500 g, 2.450 mmol), ethyl 2-chloropyrimidine-5-carboxylate (0.503 g, 2.695 mmol) and N,N-diisopropylethylamine (1.280 mL, 7.350 mmol) was dissolved in 1,4-dioxane (10 mL) at room temperature and stirred at 110 C for 18 hours, and then the temperature was lowered to room temperature to complete the reaction. After the solvent was removed from the reaction mixture under reduced pressure, the concentrate was crystallized from ethanol (5 mL) at room temperature, filtered and washed with ethanol and dried to give the title compound (0.520 g, 66.8%) as a white solid.

The synthetic route of 1009102-44-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7ClFN

3-Chloro-5-fluorobenzylamine (97 mg, 0.61 mmol) and Et3N (0.24 ml, 1.8 mmol) followed by T3P (0.6 ml, 1.8 mmol) are added at 0 C. to a solution of 3-azido-2-oxo-1-phenylpyrrolidine-3-carboxylic acid (150 mg, 0.61 mmol) in 5 ml of dichloromethane. The reaction mixture is stirred at room temperature under nitrogen for 4 hours. When the reaction is complete, water is added, and the mixture is extracted to exhaustion with dichloromethane. The combined organic phases are subsequently washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration and evaporation, the residue is purified by chromatography on silica gel, giving the product as colourless solid (150 mg, 63% yield); Thin-layer chromatogram: chloroform/methanol=9.5:0.5), Rf: 0.3 LC/MS: 388.1 (M+H at 1. 388 min); HPLC: Rt 5.12 min (HPLC purity 95.15%, 95.46%); 1H NMR (DMSO-d6, 400 MHz): delta [ppm] 9.13 (t, J=6.08 Hz, 1H), 7.70-7.68 (m, 2H), 7.43 (t, J=8.64 Hz, 2H), 7.32-7.29 (m, 1H), 7.24-7.20 (m, 2H), 7.09 (d, J=9.80 Hz, 1H), 4.42-4.34 (m, 2H), 3.95-3.89 (m, 2H), 2.61-2.58 (m, 1H), 2.28-2.22 (m, 1H).

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 90390-33-3.

Reference:
Patent; Merck Patent GmbH; Heinrich, Timo; Zenke, Frank; Calderini, Michel; Musil, Djordje; US2013/296274; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1298031-94-3,Some common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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 mixture of 8-bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1.2 g, 4.9 mmol), cyclopropylboronic acid (843 mg, 9.8 mmol), Pd(dppf)Cl2 (359 mg, 0.49 mmol) and Na2C03 (1.56 g, 14.7 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was stirred at 90 C under N2 for 48 h. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 0-35% EtOAc in petroleum ether to yield 6-chloro-8-cyclopropyl-2- methylimidazo[l,2-b]pyridazine (405 mg, 40%). MS m/z 208.0, 210.0 [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 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 16429-44-0, A common heterocyclic compound, 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, molecular formula is C6H6BrClN2, 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.

5-Bromo-3-chloro-1 ,2-diaminobenzene (4.6 g; 20 mmol; 1 eq.) is dissolved in EtOH (200 mL) and 2,3-dixydroxy-1 ,4-dioxane (2.5 g, 20 mmol; 1 eq.) is added. The mixture is stirred for 4 h at room temperature and a second portion of 2,3-dihydroxy-1 ,4-dioxane (1.3 g; 10 mmol; 0.5 eq.) is added. After stirring for 24 h at room temperature, the reaction mixture is concentrated and the residue is purified by FCC (EtOAc gradient in hexane) to provide 7- bromo-5-chloroquinoxaline as a beige solid (4.7 g; yield: 92%; UPLC purity: 98%).

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; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Malgorzata; GUZIK, Pawel Szczepan; BIA?AS, Arkadiusz Kacper; PAWLIK, Henryk Edward; BOUTARD, Nicolas Felix Pierre; (439 pag.)WO2016/180537; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 450-96-4, name is 1-Chloro-2-(trifluoromethoxy)benzene, belongs to chlorides-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 450-96-4, Computed Properties of C7H4ClF3O

Step 1 : Synthesis of INT-41 INT-41 To a solution of 1 -chloro-2-(trifluoromethoxy)benzene (2.5 mmol) in THF (10 mL) is added 2.5 M n-buthyllithium in hexanes (1 .4 mmol) at -78 C. After 40 min, a solution of DMF (2.8 mmol) in THF (2.5 mL) is added and the mixture is stirred to room overnight. The reaction is quenched with water at 0 C, extracted with EtOAc (3 x 50 mL), the combined organic layers are dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography provides 2-chloro-3- (trifluoromethoxy)benzaldehyde (INT-41 ).

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, 1-Chloro-2-(trifluoromethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; RGENIX, INC.; MARTINEZ, Eduardo, J.; KAISER, Bernd; TAVAZOIE, Sohail, F.; KURTH, Isabel; GONSALVES, Foster, Casimir; DARST, David, M., Jr.; TAVAZOIE, Masoud, Fakhr; WO2015/106164; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics