Category: chlorides-buliding-blocks

Electric Literature of 39226-96-5,Some common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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 1 1 lambda/-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-6-oxo-1-(phenylmethyl)-2- piperidinecarboxamide (E11) (in a form obtainable or prepared from L-2-amino- adipic acid)6-Oxo-1 -(phenylmethyl^-piperidinecarboxylic acid (0.117 g, 0.5 mmol, prepared according to the method described below starting from L-2-amino-adipic acid) was dissolved in dichloromethane (5 ml) and treated with N-(3-dimethylaminopropyl)-N’- ethylcarbodiimide hydrochloride (0.191 g, 1.0 mmol) and 1-hydroxybenzotriazole (0.135 g, 1.0 mmol). The mixture was stirred at room temperature for 30 minutes and then [(2-chloro-3-trifluoromethylphenyl)methyl]amine (0.209 g, 1.0 mmol) was added to the mixture and stirring at room temperature was continued overnight. The mixture was washed sequentially with water, 3N aqueous citric acid, and more water (3x), and then dried using a hydromatrix cartridge. Concentration of the organic layer gave a residue which was purified by mass-directed automated HPLC to give lambda/-{[2- chloro-3-(trifluoromethyl)phenyl]methyl}-6-oxo-1-(phenylmethyl)-2- piperidinecarboxamide. LC/MS [M+H]+ = 425/427, retention time = 2.85 minutes.; Example 19 lambda/-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-6-oxo-1-(phenylmethyl)-2- piperidinecarboxamide (E19) (in a form obtainable or prepared from D-2-amino- adipic acid)lambda/-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-6-oxo-1-(phenylmethyl)-2- piperidinecarboxamide was prepared in an analogous manner to that describedabove for Example 11 but using D-2-amino-adipic acid e.g. available from Aldrich) in the place of L-2-amino-adipic acid. LC/MS [M+H]+ = 425/427, retention time = 2.85 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/116845; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 363-51-9, name is 2-Chloro-6-fluoroaniline, 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 363-51-9, Product Details of 363-51-9

To 2-chloro-6-fluoroaniline (0.183 g, 1.259 mmol) and 2-(2-chloroquinolin-8-yl)- 6,7-dihydro-lH-pyrrolo[3,2-c]pyridin-4(5H)-one (Example 1 ; 0.075 g, 0.252 mmol) was added LHMDS (1.0 M solution in THF ; 1.259 ml, 1.259 mmol). The reaction was sealed and stirred 1 h at RT, then for 3h at 70 C. The reaction was subsequently cooled to RT and stirred overnight. 1.5 mL DMSO and 10 drops TFA were added. The mixture was filtered and purified by rpHPLC (Phenomenex Gemini 150 x 30 mm Cis column, 10-80 % ACN/H20 with 0.1 % TFA). The product-containing fractions were concentrated in vacuo, and the residue was partitioned between saturated aq. NaHCC and DCM. The aq. layer was extracted with DCM (3x), and the combined organic extracts were dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The material was dissolved in DCM/MeOH, adsorbed onto 0.75 g silica gel, and purified by silica gel chromatography using 0-50% 90/10 MeOH/DCM in DCM. The product-containing fractions were concentrated to separately afford 2-(2-((2-chloro-6-fluorophenyl)amino)quinolin-8-yl)- 6,7-dihydro-lH-pyrrolo[3,2-c]pyridin-4(5H)-one (0.022 g, 0.054 mmol, 21 % yield) as a light-yellow solid and 2-(2-((2-chloro-6-fluorophenyl)amino)quinolin-8-yl)-lH- pyrrolo[3,2-c]pyridin-4(5H)-one (0.0037 g, 9.14 muetaiotaomicron, 4%> yield) as a yellow solid. 2-(2- ((2-Chloro-6-fluorophenyl)amino)quinolin-8-yl)-6,7-dihydro-lH-pyrrolo[3,2-c]pyridin- 4(5H)-one (7): H NMR (400 MHz, DMSO-d6) delta ppm 11.82 (1 H, br. s), 9.34 (1 H, s), 8.16 (1 H, d, J=9.0 Hz), 8.01 (1 H, dd, J=7.6, 1.6 Hz), 7.55 – 7.67 (2 H, m), 7.41 – 7.54 (2 H, m), 7.28 (1 H, t, J=7.7 Hz), 7.13 (1 H, d, J=9.0 Hz), 6.83 – 6.98 (2 H, m), 3.32 – 3.44 (2 H, m), 2.43 (2 H, t, J=6.8 Hz), m/z (ESI, +ve) 406.9 (M+H)+. 2-(2-((2-Chloro-6- fluorophenyl)amino)quinolin-8-yl)-lH-pyrrolo[3,2-c]pyridin-4(5H)-one (12): H NMR (400 MHz, DMSO-de) delta ppm 12.09 (1 H, br. s), 10.68 (1 H, d, J=6.1 Hz), 9.41 (1 H, s), 8.1 1 – 8.26 (2 H, m), 7.43 – 7.76 (4 H, m), 7.34 (1 H, t, J=7.7 Hz), 7.18 – 7.25 (1 H, m), 7.14 (1 H, d, J=9.0 Hz), 6.86 – 7.00 (1 H, m), 5.91 (1 H, d, J=6.8 Hz). m/z (ESI, +ve) 405.2 (M+H)+.

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Reference:
Patent; AMGEN INC.; CEE, Victor; CHAVEZ, JR., Frank; CHEN, Jian J.; HARRINGTON, Essa Hu; HERBERICH, Bradley; JACKSON, Claire L. M.; LANMAN, Brian A.; NGUYEN, Thomas T.; NORMAN, Mark H.; PETTUS, Liping H.; REED, Anthony B.; SMITH, Adrian L.; TAMAYO, Nuria A.; TASKER, Andrew; WANG, Hui-Ling; WU, Bin; WURZ, Ryan; WO2013/130660; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 14862-52-3, 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 14862-52-3 as follows.

Nitrogen environment at biphenyl-4-ylboronic acid (100 g, 505 mmol) and tetrahydrofuran (THF) and then dissolved in 1.3 L, here 1,3-dibromo-5-chlorobenzene (150 g, 555 mmol) and tetrakis (triphenylphosphine) palladium (5.05 g, 5.84mmol) and the mixture was stirred. Into the potassuim carbonate (174 g, 1,263 mmol) in a saturated water it was heated to reflux at 80 for 7 hours. After the reaction was completed, the reaction solution into water and extracted with dichloromethane (DCM) and then water was removed with anhydrous MgSO4, filter and was concentrated under reduced pressure. Separating the thus obtained residue was refined and flashcolumnchromatography W to give the compound I-3 (149 g, 86%).

According to the analysis of related databases, 14862-52-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHEIL INDUSTRIES INC.; HAN ILL, LEE; SU JIN, HAN; YOUNG KWON, KIM; EUN SUN, YU; HO KUK, JUNG; (66 pag.)KR2015/117173; (2015); A;,
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Chlorides – an overview | ScienceDirect Topics

Reference of 96558-78-0, 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 96558-78-0 as follows.

To a solution of 3-bromo-5-chloro-aniline (150 mg, 726.5 pmol, 1 eq ), 4-pyridylboronic acid (107.2 mg, 871.9 pmol, 1.2 eq) and K2CO3 (200.9 mg, 1.5 mmol, 2 eq) in 2 mL of dioxane and 0.2 mL of H2O was added Pd(dppf)Cl2 (53.2 mg, 72.7 pmol, 0.1 eq) and purged with N2 for 3 times. The mixture was stirred at 100C for 12 hour. The reaction mixture was partitioned between 15 mL of water and 25 mL of ethyl acetate. The organic phase was separated, washed with 15 mL of brine, dried over Na2SC>4, filtered and concentrated under reduced pressure to give the crude product, which was purified by prep- TLC (S1O2, eluting with a gradient of petroleum ether:ethyl acetate =1 : 1) to give 79 mg of compound 2 (386.0 pmol, 53.1% yield) as a yellow solid.

According to the analysis of related databases, 96558-78-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AQUINNAH PHARMACEUTICALS, INC.; VACCA, Joseph, P.; WAGER, Travis, T.; (383 pag.)WO2020/117877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an argon atmosphere, 3-Bromo-6-chloroimidazo [1,2-b] pyridazine (721 mg, 3.10 mmol)Of 1,4-dioxane (25 mL),Water (5 mL)Was added 2,2,2-trifluoro-1- (4- (2-fluoro-4- (4,4,5,5-tetramethyl- 1, 3,2-dioxaborolan-2-yl) Phenyl) piperazin-1-yl) ethanone (1.50 g, 3.72 mmol),Sodium carbonate (1.15 g, 10.9 mmol),Tetrakis triphenylphosphine palladium (143 mg, 0.124 mmol) was added and degassed,Substitution with argon.Followed by stirring at 100 C. for 17 hours.After completion of the reaction,The reaction solution was made basic by adding 1 N sodium hydroxide solution,And extracted with chloroform.The organic layer was dried over anhydrous magnesium sulfate,The solvent was distilled off,And dried to give the title compound (788 mg, 77%).

The synthetic route of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YAKULT HONSHA COMPANY LIMITED; ABE, ATSUHIRO; MAE, MASAYUKI; YAMAZAKI, RYUTA; SASAI, TOSHIO; NISHIYAMA, HIROYUKI; NAGAOKA, MASATO; MATSUZAKI, TAKESHI; (47 pag.)JP6023630; (2016); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 367-21-5, name is 3-Chloro-4-fluoroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 367-21-5

To a solution of Compound 56 (5g, 34.3mmol) in dichloromethane (60mL) was added pyridine (4.2ml, 51.5mmol)under ice-cooling, dropwised a solution of bromine (1.8ml, 34.3mmol) in dichloromethane (40mL), the solution wasstirred for 1 hour. To the reaction mixture was added sodium thiosulfate aqueous solution, and extracted with ethylacetate. The organic layer was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. Theresidue was purified by silica gel chromatography (ethyl acetate / hexane) to yield Compound 57 (6.4g, yield: 83%) asan orange solid.LC-MS: m/z=223. [M+H]+

The synthetic route of 367-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Tokyo; Tohoku University; Shionogi & Co., Ltd.; NAGANO, Tetsuo; OKABE, Takayoshi; KOJIMA, Hirotatsu; KAWAGUCHI, Mitsuyasu; NUREKI, Osamu; ISHITANI, Ryuichiro; NISHIMASU, Hiroshi; AOKI, Junken; FUJIKOSHI, Chiaki; KATOU, Manabu; ODAN, Masahide; TANAKA, Nobuyuki; TATENO, Yusuke; YAMANE, Junji; (144 pag.)EP3112369; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, A new synthetic method of this compound is introduced below., SDS of cas: 1996-29-8

[0239] To a stirred solution of 1-bromo-4-chloro-2-fluorobenzene (0.9 g, 4.32 mmol) and (E)-2- (2-ethoxyvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.5 g, 7.5 mmol) in DME/H20 (v/v = 4:1, 30 mL) were added Pd(PPh3)4 (218 mg, 0.19 mmol) and Na2CO3(795mg, 7.5 mmol) under nitrogen. The reaction mixture was heated to 75C. After stirring at 75C for 12 hr, the mixture was concentrated and treated with EtOAc. The organic phase was washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the coupling product 1-(2-butoxyvinyl)-4-chloro-2-fluorobenzene which was purified by filtration through a pad of silica gel (Hex / EtOAc =20/1) to afford an oil (500 mg, 55%). The above 1-(2-butoxyvinyl)-4-chloro-2-fluorobenzene (200 mg, 0.88 mmol) was dissolved in a mixture of acetone (2 mL) and 3N aqueous HCI (2 mL). The mixture was heated at 40 C under nitrogen for 5 hours, cooled to room temperature and extracted with ether. The organic phase was washed with brine, dried over anhydrous Na2SO4, and concentrated to afford the title compound which was used in the next step without further purification (185mg). 1H NMR (400 MHz, CDCI3) 6 9.76 (s, 1H), 7.16-7.14 (m, 3H), 3.74 (s, 2H).

The synthetic route of 1996-29-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUGEN HOLDINGS (CAYMAN) LIMITED; SHAPIRO, Gideon; (157 pag.)WO2016/126869; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, 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. Formula: C8H9ClO2

General procedure: Under an argon atmosphere, Pd (dba) 2 (2.9 mg, 0.005 mmol, 0.5 mol%), phosphine compound L1 (3.4 mg, 0.006 mmol, 0.6 mol%), 1,4-dioxane was added to the reaction vessel. (0.9 mL) was added and heated to reflux for 2 minutes. The solution was mixed with 4-chlorotoluene (127 mg, 1 mmol), benzylamine (126 mg, 1.2 mmol, 1.2 equiv), NaOtBu (144 mg, 1.5 mmol, 1.5 equiv), H 2 O (14.4 muL, 0.8 mmol). , 0.8 equiv), 1,4-dioxane (2.1 mL) was added to the reaction vessel sealed. After stirring for 10 minutes at room temperature, the mixture was stirred for 1 hour under reflux. The reaction solution was passed through a short column of sodium sulfate and silica gel and then concentrated. The residue was purified by column chromatography to obtain a coupling product with a yield of 99%. The yield of diarylate was less than 1%.

The synthetic route of 1-Chloro-3,5-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Otsuka Research Institute; Sai, Masahiro; (15 pag.)JP2019/189569; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, 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. Computed Properties of C6H5BrClN

To a solution of 5-bromo-2-chloroaniline (2.06 g, 9.88minol) in propane-1,2,3-triol (4.23 g, 45.90 minol) was added FeSO4.7H20 (520 mg, 1.87 minol) and sulfuric acid (3 g, 29.67 minol) at room temperature. The resultingminxture was stirred for 4 h at 120 ¡ãC. After cooling to room temperature, the reactionminxture was adJusted to pH 13 using sodium hydroxide solution (2 M). The resultingminxture was extracted with ethyl acetate (50 mL x 3). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (0percent to 94percent gradient) to yield 5-bromo-8-chloroquinoline as yellow solid (760 mg, 32percent). MS: m/z = 243.8 [M+Hj.

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

Reference:
Patent; MERCK PATENT GMBH; SHERER, Brian A.; BRUGGER, Nadia; (546 pag.)WO2017/106607; (2017); A1;,
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. 344-19-4, name is 2,6-Dichloro-4-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H4Cl2FN

PREPARATION OF 2,6-DICHLORO-4-FLUOROPHENYLHYDRAZINE (INTERMEDIATE NO. 2) 9.0 g (0.05 mol) of 2,6-dichloro-4-fluoroaniline was added to 50 ml of concentrated hydrochloric acid, and a solution of 3.8 g (0.055 mol) of sodium nitrite in 25 ml of water was dropwise added thereto at a temperature of from 0 to 5 C. After completion of the dropwise addition, the mixture was stirred at the same temperature for further 1 hour. Insolubles were removed by filtration, and the filtrate was dropwise added at a temperature of from 0 to 10 C. to a solution of 33.8 g (0.15 mol) of stannous chloride dihydrate in 50 ml of concentrated hydrochloric acid. After completion of the dropwise addition, the mixture was stirred at the same temperature for further 2 hours. The precipitated hydrochloride was collected by filtration, and 50 ml of water was added thereto. The mixture was made alkaline with an addition of 20% sodium hydroxide, and the precipitated solid was extracted with ethyl ether. The ethyl ether layer was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The residue thereby obtained was washed with cold n-hexane to obtain 6.9 g (yield: 70.4%) of the desired compound as white feather-like crystals. Melting point: 117-119 C.

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 344-19-4.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US4925864; (1990); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics