Month: March 2021

Some common heterocyclic compound, 4152-90-3, name is (3-Chlorophenyl)methanamine, molecular formula is C7H8ClN, 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 C7H8ClN

To a mixture of 6-bromo-2,4-dichloroquinazoline (278 mg, 1.0 mmol) and (3-chlorophenyl)methanamine (142 mg, 1.0 mmol) in THF (2 ml) was added Et3N (0.209 ml, 1.5 mmol). The mixture was stirred at rt for 1 h. The mixture was poured into EtOAc/H2O (5 mL/5 mL). The aqueous layer was extracted with EtOAc (3 mL x 2). The combined organic layer was dried (Na2SO4) and filtered. After removal of solvent, the product was triturated with hexane and dried to give 6-bromo-2-chloro-N-(3-chlorobenzyl)quinazolin-4-amine (360 mg, 0.94 mmol, 94 percent yield) as a white solid. LC-MS (Method 1): tR = 3.69 min, m/z (M+H)+ = 384.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4152-90-3, its application will become more common.

Reference:
Article; Yang, Shyh-Ming; Urban, Daniel J.; Yoshioka, Makoto; Strovel, Jeffrey W.; Fletcher, Steven; Wang, Amy Q.; Xu, Xin; Shah, Pranav; Hu, Xin; Hall, Matthew D.; Jadhav, Ajit; Maloney, David J.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 21; (2018); p. 3483 – 3488;,
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These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, 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. name: 4-Chloro-3-fluoroaniline

To a solution of 1005 (10.0 g, 68.7 mrnol) in heptane (100 ml) was added(Boc)20 (16.4 rnL, 76.6 rnmol) After stirring the reaction mixture at 80C for 16 h, solvent wasevaporated and the residue was purified by Comhiflash column chromatography (hexane/EtOAc, 1:2) to afford 1006 (7.0 g, 43%) as a solid. 1H NMR (400 MHz, CDC13): oe 7.44 (dd, 1H), 727 (t, IH), 694 (dd, 1H), 6.53 (s, 1H). 1.50 (s, 9H).

The synthetic route of 4-Chloro-3-fluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IOMET PHARMA LTD.; MERCK SHARP & DOHME CORP.; COWLEY, Phillip, M.; HAN, Yongxin; (67 pag.)WO2017/48612; (2017); A1;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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;,
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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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