Tag: M.W=200-300

Reference of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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 solution of 3,5-difluorobenzenesulfonyl chloride (1.1 eq., 2.62 g) in dry dichloromethane (15 mL) was added dropwise to a stirred solution of 3-[4-(4-methyl- piperazin- 1 -yl)-2-nitro-benzoylamino]-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridine- 1 – carboxylic acid ethyl ester dihydrochloride (5.7g, 10.85 mmol) and N,N- diisopropylethylamine (6 eq., 11.34 mL) in dry dichloromethane (100 mL) at room temperature. Stirring was continued for 20 hours. The reaction mixture was then washed with water (2×80 mL), saturated sodium hydrogenocarbonate (2×80 mL), brine (80 mL), dried over sodium sulfate, evaporated to dryness and purified by flash chromatography on silica gel, using acetone-dichlorometane 60:40 as eluant. The title compound was obtained as yellow powder (5g, 73% yield).IH-NMR (400 MHz), delta ppm, DMSOtZ6): 11.21 (s, IH), 7.67 (m, 2H), 7.54 (m, 2H), 7.44 (d, J2=2.44 Hz, IH), 7.27 (dd, Jl=8.78 Hz, J2=2.44 Hz, IH), 4.37 (q, J=7.07 Hz, 2H), 4.14 (s, 2H), 3.55 (m, 2H), 3.34 (m, 4H), 3.02 (m, 2H), 2.52 (m, 4H), 2.25 (s, 3H), 1.33 (t, J=7.07 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Difluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68619; (2007); 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrClN3

Intermediate P3-Bromo-6-(3-chlorophenoxy)imidazo[1,2-b]pyridazineVariant 3: 5 g (21.5 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine, 3 g (23.7 mmol) of 3-chlorophenyl, 246 mg (0.27 mmol) of tris(dibenzylidineacetone)dipalladium, 500 mg of rac-BINAP and 4.1 g of sodium tert-butoxide are stirred in a mixture of 100 ml of dimethylformamide and 200 ml of tetrahydrofuran at 100 C. under a protective gas atmosphere for 12 h.The reaction mixture is then mixed with saturated sodium chloride solution. The aqueous phase is extracted with ethyl acetate. The organic phase is washed twice with dilute aqueous NaCl solution and once with saturated aqueous NaCl solution and dried over sodium sulfate. In the final purification by chromatography on silica gel, 2.78 g (40%) of the desired product were isolated.1H-NMR (DMSO-D6): delta=7.22 (d, 1H); 7.31-7.42 (m, 2H); 7.51 (d, 1H); 7.55 (t, 1H); 7.83 (s, 1H); 8.25 (d, 1H) ppm.MS (ESI): m/z=324/326 [M+H]+

According to the analysis of related databases, 13526-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRIEN, Olaf; Eis, Knut; Bader, Benjamin; Guenther, Judith; Von Bonin, Arne; US2009/93475; (2009); 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. 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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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,
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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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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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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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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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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, 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