Author: Jessica.F

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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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)+.

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; 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;,
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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,
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Adding a certain compound to certain chemical reactions, such as: 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, 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 14752-66-0, Recommanded Product: 14752-66-0

In a dry test tube, add 34mg and 198mg pyrazole of chlorobenzene sulfinateSodium, added 267mg of NBS. 2mL ethyl acetate was then added to dissolve the solid, the reaction solution was stirred at 25 12 hours. After completion of the reaction, ethyl acetate and water extraction, the resulting organic phase was concentrated on a rotary evaporator, silica gel column (ethyl acetate and petroleum ether, the volume ratio of 1: 3) to give the product 109mg, yield 68% , the following reaction formula:

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; Wenzhou Medical College; Xia, Qinqin; Fu, Lili; Bao, Xiaodong; Liu, Zhiguo; Liang, Guang; (11 pag.)CN105693621; (2016); A;,
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Electric Literature of 220227-21-4,Some common heterocyclic compound, 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, molecular formula is C6H2ClF3O2S, 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.

Synthesis of N-{5-[l-(2,4-Dichloro-benzyl)-5-fluoro-3-methyl-lH-indol-7-yl]- [l,3,4]oxadiazol-2-yl}-2,4,5-trifluoro-benzenesulfonamide, B12. A solution of 2,4,5-trifluorobenzenesulfonyl chloride (92 mg, 0.4 mmol, 4 equiv.) in pyridine (0.3 mL) was added to a mixture of 1-14 (39 mg, 0.1 mmol, 1 equiv.) and DMAP (49 mg, 0.4 mmol, 4 equiv.) at rt. The reaction mixture was heated to 90 0C for 2 h. The reaction mixture was then quenched with 10% aqueous HCl and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting oil was chromatographed on SiO2 (0.5 g), eluting with CH2Cl2 to afford B12 (10 mg, 17 %) as a yellow oil. Rf= 0.40 (EtOAc). 1H-NMR (400 MHz, CDCl3) 2.34 (d, J =1.2 Hz, 3H), 5.64 (s, 2H), 6.05 (d, J = 8.4 Hz, IH), 6.97 (dd, J = 8.4, 2.0 Hz, IH),7.03 (s, IH), 7.08 (m, IH), 7.29 (dd, J = 9.6, 2.4 Hz, IH), 7.35 (d, J = 2.0 Hz, IH), 7.51 (dd, J = 8.4, 2.4 Hz, IH), 7.86 (m, IH). LC-MS (95 %): ESI” Calcd. 586 (M) Found: 585.1 (M-I).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4,5-Trifluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; DECODE CHEMISTRY, INC.; WO2006/44405; (2006); 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. 1205-71-6, name is 4-Chloro-N-phenylaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1205-71-6

To a solution of 4-chloro-A/- phenylaniline 1 (0.2 g, 0.98 mmol) in dry DCM (3 mL) at 0 C was added triphosgene (0.32 g, 1 .08 mmol). Pyridine (0.1 1 mL, 1 .38 mmol) predissolved in 1 mL of DCM was added slowly to the reaction mixture. The reaction was stirred for another 15 min and then warmed to RT and stirred for 2 h. It was quenched under cooling by the slow addition of water (the solution turned pink). The mixture was extracted and the aqueous layer was washed again with DCM. The combined organic extracts were washed with brine, dried over MgS04, concentrated to give 0.24 g (92%) of the title compound as a peach colored solid. This was used in the next step without further purification. 1H NMR (400 MHz, Chloroform-d) d 7.47 – 7.27 (m, 9H).

According to the analysis of related databases, 1205-71-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; HOLINSTAT, Michael; ADILI, Reheman; WHITE, Andrew; (43 pag.)WO2019/204447; (2019); A1;,
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Some common heterocyclic compound, 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, molecular formula is C8H17Cl2N, 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. Recommanded Product: 26487-67-2

Compound 4 (200mg, 0.75mmol) refluxed with K2CO3 (259.42mg, 1.87mmol), 1-(2-Chloro-ethyl)-azepane hydrochloride (148.58mg, 0.75mmol) in acetone furnished 7 (220mg, 75percent) as brown viscous oil. 1H NMR (300MHz, CDCl3): delta 7.21?7.06 (m, 8H), 6.91?6.78 (m, 3H), 6.64?6.63 (m, 1H), 5.59 (s, 1H), 4.07 (t, J=6.0, 2H), 2.97 (t, J=6.1, 2H), 2.81 (t, J=5.6, 4H), 1.69?1.61 (m, 8H); 13C NMR (CDCl3, 50MHz): delta 157.5, 148.4, 144.1, 136.2, 129.8 (2C), 128.7 (2C), 128.4 (2C), 126.6, 126.5, 126.2, 124.4, 114.4 (2C), 65.7, 57.8, 54.9 (2C), 51.3, 25.7 (3C), 24.1; IR (Neat): 3019, 2938, 2362, 1610, 1509, 1218, 763cm?1; MS (ESI): m/z 392 (M+H)+; Anal. Calcd for C25H29NOS: C, 76.68; H, 7.46; N, 3.58. Found: C, 76.72; H, 7.39; N, 3.61.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 26487-67-2, its application will become more common.

Reference:
Article; Singh, Priyanka; Manna, Sudipta Kumar; Jana, Amit Kumar; Saha, Tiash; Mishra, Pankaj; Bera, Saurav; Parai, Maloy Kumar; Srinivas Lavanya Kumar; Mondal, Sankalan; Trivedi, Priyanka; Chaturvedi, Vinita; Singh, Shyam; Sinha, Sudhir; Panda, Gautam; European Journal of Medicinal Chemistry; vol. 95; (2015); p. 357 – 368;,
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Reference of 7051-16-3, A common heterocyclic compound, 7051-16-3, name is 1-Chloro-3,5-dimethoxybenzene, molecular formula is C8H9ClO2, 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.

General procedure: In a microwave vial equipped with a stirring bar, potassium N-methyltrifluoroborate isoindolin-1-one (6) (80.1 mg, 0.316 mmol), potassium carbonate (104 mg, 0.752 mmol), Pd(MeCN)2Cl2 (4.9 mg, 7.5 mol%), and XPhos (17.9 mg, 15.0 mol%) were successively introduced. The vial was capped and put under inert atmosphere (3 x vacuum/N2 cycles). The electrophile was then introduced using a microsyringe (0.25 mmol, 1.0 equiv.) followed by 0.8 mL of degassed t-BuOH and 0.2 mL of degassed distilled water. The resulting mixture was then placed in an oil bath or a hotplate-magnetic stirrer system preheated at 100 C and stirred at this temperature overnight (reactions followed by thin-layer chromatography, TLC). After cooling to room temperature, the vial was uncapped and the reaction mixture was diluted with dichloromethane (DCM) (5 mL) and water (5 mL). The aqueous layer was extracted with dichloromethane (3 x 15 mL). Organic layers were combined, washed with brine solution, and dried over Na2SO4, and the solvent was removed under vacuum to yield the crude product. The crude product was purified by flash column chromatography on silica gel using 30% ethyl acetate/hexane as the eluent.

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:
Article; Nadaf, Rashid N.; Seapy, Dave G.; Synthetic Communications; vol. 44; 14; (2014); p. 2012 – 2020;,
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