Author: Jessica.F

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., Product Details of 1996-29-8

A 3L 3-neck round bottom flask equipped with a mechanical stirrer, a temperature controller, and a nitrogen inlet was charged with potassium tert-butoxide (Aldrich 95%, 84.6 g, 0.716 mol) and DMSO (400 mL, 4×) at room temperature and stirred for 15 minutes. To this solution was added pyrazole 2 (59 g, 0.719 mol) followed by a DMSO rinse (50 mL, 0.5×). The resulting orange turbid solution was stirred for 15 minutes and fluoride 1 (100 g, 0.477 mol) was added followed by a DMSO rinse (50 mL, 0.5×). This mixture was then heated to 50 C. and held for 5 hours at this temperature. After cooling to room temperature, the reaction mixture was diluted with MTBE (750 mL), and water (500 mL) was added to give a brown turbid mixture. After 15 minutes stirring, the organic layer was separated and sequentially washed with 1 N HCl (250 mL), brine (250 mL), and water (250 mL). Solution assay of organic layer was carried out using GC (conversion >99%, solution yields of 3 and its regioisomer 4 were 83% and 17%, respectively). The MTBE solution was then concentrated under vacuum to a total volume of about 200 mL (KF showed 0.737% water). THF (500 mL) was added, and concentrated to 2× solution (KF=0.158%). THF addition-concentration sequence was repeated to give a 2× solution (KF=0.023%), which used directly in the next step.Analytical samples of compounds 3 and 4 were purified by column chromatography and characterized: Compound 3: white crystals; M.p.: 76 C. (DSC onset temperature). 1H NMR (400 MHz, CDCl3) delta 7.80 (1H, d, J=2.3 Hz), 7.61 (1H, d, J=8.6 Hz), 7.58 (1H, d, J=2.5 Hz), 7.22 (1H, dd, J=8.6, 2.6 Hz), 6.27 (1H, d, J=2.5 Hz), 2.38 (3H, s); 13C NMR (100 MHz, CDCl3) delta 150.8, 140.6, 134.6, 134.1, 132.0, 129.0, 128.2, 115.4, 107.0, 13.6. Compound 4: white crystals; 1H NMR (400 MHz, CDCl3) delta 7.65 (1H, d, J=8.6 Hz), 7.62 (1H, d, J=1.5 Hz), 7.43 (1H, d, J=2.5 Hz), 7.35 (1H, dd, J=8.6, 2.2 Hz), 6.21 (1H, s), 2.19 (3H, s); 13C NMR (100 MHz, CDCl3) delta 140.6, 140.2, 140.0, 134.1, 133.9, 130.8, 130.2, 120.7, 105.9, 11.4.

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; Bednarz, Mark S.; Burgoon, JR., Hugh Alfred; Iimura, Shinya; Kanamarlapudi, Ramanaiah C.; Song, Qiuling; Wu, Wenxue; Yan, Jie; Zhang, Haiming; US2009/62540; (2009); A1;,
Chloride – Wikipedia,
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Reference of 13526-66-4, 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 13526-66-4 as follows.

Synthesis of intermediate IV-02IV-01 IV-02To a solution of 3-bromo-6-chIoroimidazo[1 ,2-b]pyridazine (IV-01) (450 mg, 1.936 mmol) in 1 ,4-dioxane (8 mL) was added 3-(N-Boc-aminomethyl)pyridine-5- boronic acid pinacol ester (679 mg, 2.033 mmol), aq. Na2C03 2 (3 mL, 6 mmol) and PdCI2(PPh3)2 (136 mg, 0.194 mmol). The resulting mixture was heated at 80 C in a sealed tube for 8 h. On cooling, the mixture was diluted with DC and water. Layers were separated and the aqueous phase was extracted twice with DCM. The combined organic extracts were dried (Na2S04), filtered and concentrated. The residue was purified by flash chromatography (Biotage) using MeOH:DCM 0:100 to 20:80 as eluent to afford intermediate IV-02 (525mg, 75%).

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; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; ALVAREZ ESCOBAR, Rosa Maria; RIESCO FAGUNDO, Rosario Concepcion; GARCIA GARCIA, Ana Belen; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; BLANCO APARICIO, Carmen; CEBRIAN MUNOZ, David Alvaro; WO2012/156756; (2012); A2;,
Chloride – Wikipedia,
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These common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, 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. SDS of cas: 2533-69-9

A solution of aniline of preparation 28 (79 mg, 0.56 mmol) in acetic acid (3 ml) was treated with methyl-2,2,2-trichloroacetimidate (77 mul, 0.62 mmol) and the resulting solution was left to stir at room temperature for 16 hours. Water (10 ml) was added and the reaction stirred for a further hour. The precipitate was filtered off and dried in vacuo. The resulting solid was suspended in a mixture of acetonitrile and water (3:1 by volume, 4 ml) and treated with a solution of (3aR,6aS)-2-methyloctahydropyrrolo[3,4-c]pyrrole (148 mg, 1.17 mmol) in a mixture of acetonitrile (0.75 ml) and water (0.25 ml). After 3 hours the solvent was removed in vacuo and the residue dissolved in dichloromethane (15 ml), washed with saturated sodium bicarbonate (2*15 ml), dried (sodium sulfate) and concentrated in vacuo. Purification by flash column chromatography on silica gel eluding with dichloromethane:methanol:880 ammonia (99:1:0.1 changing to 93:7:0.7, by volume) gave the title compound as a colourless solid (133 mg). 1H NMR (400 MHz, CD3OD): delta 7.19 (1H, s), 6.87-6.84 (1H, d), 4.39-4.27 (2H, m), 3.90-3.84 (1H, m), 3.75-3.71 (1H, m), 3.09-2.95 (2H, m), 2.79-2.72 (2H, m), 2.51-2.40 (2H, m), 2.46 (3H, s), 2.33 (3H, s) ppm. MS (APCI): m/z 303 [M+H]+, 301 [M-H]-

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

Reference:
Patent; Lane, Charlotte Alice Louise; Price, David Anthony; US2006/111416; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 102-49-8, name is 3,4-Dichlorobenzylamine, molecular formula is C7H7Cl2N, 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: 3,4-Dichlorobenzylamine

Methyl 6-(3,4-dichlorobenzylamino)nicotinate A mixture of (3,4-dichlorophenyl)methanamine (1.010 mL, 7.58 mmol), TEA (1.218 mL, 8.74 mmol), and methyl 6-chloronicotinate (1 g, 5.83 mmol) in ethanol (29 mL) was heated at 120° C. for 5 min in a microwave oven. The reaction mixture was further heated at 100° C. for 54 h, then concentrated. The residue was purified by flash chromatography on silica gel using 5-35percent ethyl acetate in hexanes. The desired fractions were concentrated to give methyl 6-(3,4-dichlorobenzylamino)nicotinate as a pale yellow solid (0.55 g, 33percent). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 8.77 (1H, s), 8.01 (1H, dd, J=8.78, 2.01 Hz), 7.33-7.52 (2H, m), 7.19 (1H, d, J=8.03 Hz), 6.37 (1H, d, J=8.78 Hz), 5.37 (1H, br. s.), 4.58 (2H, d, J=6.02 Hz), 3.88 (3H, s). LCMS: R.T.=2.81; [M+H]+=311.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 102-49-8, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; King, Dalton; Macor, John E.; Olson, Richard E.; Iwuagwu, Christiana I.; Karageorge, George N.; US2013/79338; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 918538-05-3,Some common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, molecular formula is C6H3Cl2N3, 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; 2-(4-(3-Cyclopropyl-l/f-pyrazol-5-ylamino)pyrrolo[l,2-fJ[l,2,4]triazin-2-yl)- lambda-(6-fluoropyridin-3-yl)pyrazolidine- 1 -carboxamide IA. 2-Chloro-N-(3 -cyclopropyl- lH-pyrazol-5-yl)pyrrolo [ 1 ,2-f] [ 1 ,2,4]triazin-4- amine [00146] A mixture of 2,4-dichloropyrrolo[l,2-f][l,2,4]triazine (977 mg, 5.2 mmole), S-cyclopropyl-lH-pyrazoW -amine (640 mg, 1 equiv), and diisopropylethylamine (1.54 mL, 1.7 equiv) in isopropyl alcohol (5 mL) was stirred at room temperature overnight. The product was collected by filtration (1.18 gm, 83% yield): MS: 275 (M+eta)~; HPLC Ret Time: 1.56 min. (Phenomenex-Luna s 10 3.0 x 50 mm column, 3 min gradient, 4 mL/min).

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-Dichloropyrrolo[2,1-f][1,2,4]triazine, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2009/111531; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 98446-49-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 98446-49-2 name is 2,4-Dichloro-5-methoxyaniline, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 68 4-(2,4-Dichloro-5-methoxyphenylamino)benzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile A mixture of 230 mg (1.2 mmol) of 2,4-dichloro-5-methoxyaniline (WO 8501939A1) and 48 mg (1.2 mmol) of 60% sodium hydride in mineral oil in 10 mL of tetrahydrofuran is heated at reflux temperature. The reaction mixture is cooled and 200 mg (0.82 mmol) of 4-chlorobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile is added. The mixture is heated at reflux for 4 hours, then cooled to room temperature and partitioned between ethyl acetate and water. The organic layer is washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether is added to the residue and the resultant solid is collected by filtration and purified by column chromatography, eluding with 3:1 hexane/ethyl acetate, to provide 89 mg (27%) of a white solid, mp 234-236 C. 1H-NMR (DMSO-d6): delta 3.86 (s, 3H), 7.21 (s, 1H), 7.56-7.67 (m, 2H), 7.78 (s, 1H), 8.07 (d, 1H), 8.37 (d, 1H), 8.79 (s, 1H), 9.79 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dichloro-5-methoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; American Home Products Corporation; US2001/51620; (2001); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 870-24-6, name is 2-Chloroethanamine hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 870-24-6

In a 500 ml four-necked flask,343 parts of dimethylformamide,31.6 parts of triethylamine and 2-chloroethylamine hydrochloride(Manufactured by Tokyo Chemical Industry Co., Ltd.) 33.2 parts, and the mixture was stirred for 10 minutes. 49.6 parts of p-toluenesulfonyl chloride (manufactured by Tokyo Chemical Industry Co., Ltd.)Was added little by little so that the liquid temperature did not exceed 20 C.,And the mixture was stirred at room temperature for 3 hours.The reaction solution was poured into cooled 5% aqueous hydrochloric acid,After stirring for 15 minutes, the precipitated crystals were collected by filtration, washed,By drying,33.8 parts of a dye intermediate represented by the following formula (101) was obtained.

The synthetic route of 870-24-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIPPON KAYAKU COMPANY LIMITED; MIFUJI, AKIHIRO; SUZUKI, SAORI; MORITA, RYOUTARO; (29 pag.)JP2018/53152; (2018); A;,
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. 54788-38-4, name is 2-Chloro-4-methoxy-1-methylbenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 54788-38-4

General procedure: To anhydrous THF (6.4 mL) in a dry round-bottom flask was added nickel(II)bromide (279 mg, 1.28 mmol), zinc powder (250 mg, 3.83 mmol), and triphenylphosphine (1.68 g, 6.39 mmol). The mixture was heated to 50 C and stirred for 30 min. The selected o-chlorotoluene (8a or 8b, 12.78 mmol) was added, the temperature raised to 60 C, and the reaction was tightly capped and allowed to stir 30 min, then potassium cyanide (1.66 g, 25.5 mmol) was added over the course of 5 h in 2 equal portions. The mixture was allowed to stir an additional 16 h. Water was added to quench the reaction, and the suspension extracted 3× with ether. The resulting organic layer was washed with H2O and brine, dried over MgSO4, filtered, and concentrated to a heterogeneous mixture of white crystals and clear oil. The residue was diluted with 10 mL of toluene, then methyl iodide (997 mg, 7.02 mmol) was added and allowed to stir 16 h at room temperature. The resulting white crystals were removed via vacuum filtration. The filtrate was concentrated in vacuo to a clear oil. Flash chromatography with 2% EtOAc/hex delivered the pure product in 68-90% yield.

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; Yestrepsky, Bryan D.; Xu, Yuanxi; Breen, Meghan E.; Li, Xiaoqin; Rajeswaran, Walajapet G.; Ryu, Jenny G.; Sorenson, Roderick J.; Tsume, Yasuhiro; Wilson, Michael W.; Zhang, Wenpeng; Sun, Duxin; Sun, Hongmin; Larsen, Scott D.; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1880 – 1897;,
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. 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, A new synthetic method of this compound is introduced below., Application In Synthesis of 3,6-Dichloro-1,2,4,5-tetrazine

General procedure: To a solution of DIPEA (2.1 mmol) in acetonitrile (150 mL) which was preheated to 70 C was added dropwise a solution of 3,6-dihydroxyphthalimide derivatives 1a-e (1 mmol) and 3,6-dichlorotetrazine (2, 1 mmol) in acetonitrile (25 mL) during 25 min. After being stirred for another 5 min, the reaction was quenched by cooling down the mixture to ambient temperature and adding water (200 mL). The resulting mixture was neutralized with dilute hydrochloric acid (1 M) and extracted with EtOAc (3 × 150 mL). The combined organic solution was washed with brine (3 × 200 mL) and then dried over anhydrous Na2SO4. After filtration and concentration, the residue was chromatographed on a silica gel column using a mixture of DCM and EtOAc (v/v = 100:1) as an eluent to give product 3a-e. 3a: 140 mg, yield 42%, red solid, mp 275 C (decomp.);1H NMR (400 MHz, acetone-d6, 25 C) delta 8.00 (s, 6H),7.20-7.34 (m, 15H); 13C NMR (101 MHz, acetone-d6, 25 C) delta168.8, 164.4, 147.1, 132.2, 132.1, 129.6, 128.8, 127.5, 125.6;IR (KBr, cm-1) nu: 3078, 1777, 1724, 1494, 1384, 1230, 1115,955; HRMS-APCI: [M + H]+ calcd for C48H22N15O12,1000.1567; found, 1000.1553; anal. calcd for C48H21N15O12:C, 57.66; H, 2.12; N, 21.01; found: C, 57.71; H, 2.08; N, 20.70.

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; Gu, Meng-Di; Lu, Yao; Wang, Mei-Xiang; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1976 – 1983;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, 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 C6H4ClN3

478 mg (3.1 1 mmol) of 6-chloroimidazo[1 ,2-b]pyridazine were introduced into 10 mL of chloroform under argon and, while cooling in ice, 664 mg (3.73 mmol) of N- bromosuccuinimide were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The reaction mixture was then mixed with water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with brine and dried over sodium sulfate. In the final removal of the solvent in vacuo, the desired product was isolated in quantitative yield in the form of an amorphous white solid which was employed without further chromatographic purification in subsequent reactions.

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

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; HAeGEBARTH, Andrea; PETERSEN, Kirstin; BOeMER, Ulf; WO2013/149909; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics