Tag: M.W=200-300

Some common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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. Application In Synthesis of 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine

8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (500 mg, 2.05 mmol, prepared according to example 43) was combined with vinylboronic acid pinacol ester (0.43 mL, 2.3 mmol), Pd(dppf)Cl2 (150 mg, 0.21 mmol) and K2C03 (850 mg, 6.15 mmol) in 1,4-dioxane (10 mL) and H20 (2 mL). The mixture was stirred at 90 C for 2 h under N2. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 10-20% EtOAc in petroleum ether to yield 6-chloro-2-methyl-8-(prop- l-en-2-yl)imidazo[l,2- b]pyridazine (300 mg, 77%). MS m/z 208.0, 210.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1298031-94-3, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
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102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: chlorides-buliding-blocks

To each of 2 ice/water cooled flasks, containing 4-bromo-5-chloro-2-methoxyaniline (120 g, 507.42 mmol) in DCM (1000 mL) was added boron tribromide (382 g, 1522.26 mmol). After addition, the mixture was warmed to room temperature and stirred for 2 h. The reactionmixtures were poured into ice/water (2L), basified with solid sodium bicarbonate to pH 7 and extracted with ethyl acetate (l000mL x 6). The combined organics were dried over sodium sulphate and the solvent removed to give 2-amino-5-bromo-4-chlorophenol as a brown solid (220 g).LCMS: Rt 1.35 mi MH 222/224.

The synthetic route of 102170-53-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BOUILLOT, Anne Marie Jeanne; DENIS, Alexis; LIDDLE, John; MIRGUET, Olivier; WALKER, Ann, Louise; (64 pag.)WO2016/188827; (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. 208186-78-1, name is 1,2-Dibromo-5-chloro-3-fluorobenzene, A new synthetic method of this compound is introduced below., Safety of 1,2-Dibromo-5-chloro-3-fluorobenzene

GammaAlpha1 2-Bromo-4-chloro-6-fluoro-benzaldehydeTo a solution of l,2-dibromo-5-chloro-3-fluoro-benzene (10 g, 34.68 mmol) in heptane (27 ml) was added THF (44 ml) and the mixture was cooled to -45 C. Then, iPrMgCl (38.14 ml, 38.14 mmol, 1M solution in THF) was added dropwise to the reaction mixture maintaining the temperature between -40 C to -45 C. The mixture was stirred for 30 minutes at -40 C before DMF (13.4 ml, 173.4 mmol) was added dropwise to the reaction mixture maintaining the temperature between -45 C to -20 C. After stirring for another 15 minutes at -20 C, it was poured into a mixture of 2N HC1 (20 ml) and ether (50 ml) at 0 C. The organic layer was separated and the aqueous layer was extracted two times with ether. The combined organic layers were dried with Na2S04 and evaporated in vacuo to obtain the title compound (7.8 g, 95%) as yellow solid.

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; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; BINGGELI, Alfred; HERTEL, Cornelia; KONKAR, Anish Ashok; KUEHNE, Holger; KUHN, Bernd; MAERKI, Hans P.; WANG, Haiyan; WO2012/101011; (2012); A2;,
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Synthetic Route of 16429-44-0, 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. 16429-44-0, name is 5-Bromo-3-chlorobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows.

5-bromo-3-chloro-1 ,2-diaminobenzene (4.6 g; 20 mmol; 1 .0 eq.) was dissolved in EtOH (200 ml_) and then 2,3-dihydroxy-1 ,4-dioxane (2.5 g, 20 mmol; 1 .0 eq.) was added. The mixture was stirred for 4 h at RT and a second portion of 2,3-dihydroxy-1 ,4-dioxane (1 .3 g; 10 mmol; 0.5 eq.) was added. After stirring for 24 h at rt, RM was concentrated in a rotary evaporator and the residue was purified by FCC to provide 7-bromo-5- chloroquinoxaline (Intermediate 3) as a beige solid (4.7 g; yield 92 %; 98 % by UPLC).

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-3-chlorobenzene-1,2-diamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK PATENT GMBH; BUCHSTALLER, Hans-Peter; (101 pag.)WO2018/87021; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 54773-19-2,Some common heterocyclic compound, 54773-19-2, name is 1,2-Dichloro-3-(trifluoromethyl)benzene, molecular formula is C7H3Cl2F3, 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.

2,3-dichlorobenzotrifluoride 215 g (1.00 mol) of the compound of the formula (II), anhydrous potassium fluoride 140 g (2.41 mol), sulfolane 2000 mL,10 g of tetraphenylphosphonium bromide was introduced into the autoclave in batches, and the temperature was raised to 250-300 C for 20 hours under stirring. After cooling, the formed potassium chloride and excess potassium fluoride were removed by filtration.The filtrate is rectified, and a fraction of 112 C to 119 C is collected to obtain a compound of formula (III) 2,3-difluorobenzotrifluoride; The residue is further subjected to rectification to collect a fraction of 145 C – 151 C to obtain a by-product 2-fluoro-3-chlorobenzotrifluoride; the by-product can be recycled.The average yield of 2,3-difluorobenzotrifluoride, which is a continuous preparation of the compound of formula (III) after application, is 87.6%.

The synthetic route of 54773-19-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Zheng Rong Pharmaceutical And Chemical Co., Ltd.; Chen Zhengwei; Xiao Tao; Zhu Jiahao; Yu Chuanzong; Dai Jianxin; (13 pag.)CN104693080; (2016); B;,
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Related Products of 64473-35-4, 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. 64473-35-4 name is 1-(3-Bromopropyl)-4-chlorobenzene, 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.

Step 1 3-(4-Chlorophenyl)propylamine The potassium salt of phthalimide (4.4 g, 24 mmol) was dissolved in DMF (20 ml) and 1-chloro-4-(3-bromopropyl)benzene (4.67 g, 20 mmol) was added. The mixture was stirred at 80 C. for 16 hours. Water (50 ml) and DCM (50 ml) were added, the phases were separated and the aqueous phase extracted with DCM (2*50 ml). The combined organic phases were washed with sodium hydroxide (0.2 M, 50 ml), dried (magnesium sulphate), filtered and concentrated in vacuo. Ethanol (75 ml) and hydrazine hydrate (2 equiv.) were added and the mixture was heated to reflux for 2 hours. After cooling the mixture was filtrated and the filter cake washed with DCM (2*50 ml). The filtrate and washings were evaporated and dissolved in ethyl acetate (40 ml). Washing of the organic phase with sodium hydroxide (0.4 M, 2*25 ml) and water (2*25 ml) followed by drying (magnesium sulphate), filtration and evaporation gave 3-(4-chlorophenyl)propylamine. 1H NMR (CDCl3): delta1.82-1.50 (m, 4H); 2.78-2.53 (m, 4H); 7.32-6.96 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(3-Bromopropyl)-4-chlorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Andersen, Knud Erik; Dorwald, Florencio Zaragiza; Peschke, Bernd; Sidelmann, Ulla Grove; Rudolf, Klaus; Stenkamp, Dirk; Hurnaus, Rudolf; Muller, Stephan Georg; Krist, Bernd; Eriksen, Birgitte; US2002/58659; (2002); A1;,
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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. 167404-32-2, name is 4-Cyclopropylbenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Cyclopropylbenzene-1-sulfonyl chloride

In a flame dried flask under N2 blanket, compound D (1.5 g, 4.9 MMOL) was dissolved in dry THF (30 mL) and COOLED TO-78C. N-BUTYL lithium (1.9 M in hexanes, 5.4 mL, 9.7 MMOL) was added followed after 45 min by compound E (1.27 g, 6.3 MMOL). The cold bath was removed after 2 h and the reaction mixture was allowed to warm to rt over 45 minutes then quenched with aq NH4CI. EtOAc (30 mL) was added to dilute the reaction mixture. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (25% EtOAc/Hexanes) to give 545 mg (27%) of compound F. Compound i (120 g, 1.0 mml) was dissolved in CH2CI2 (1.2 L) with HG20 (6.0 g, 14.4 MMOL) and K2CO3 (24.0 g, 0.17 mol) and cooled to-30 C. Br2 (85.2 g, 1.1 mol) was added over 10 min period of time. The reaction mixture was stirred at-30 C for 4.5 h. The reaction mixture was washed with H20 (1 L) and brine (1 L). The organic layer was dried over NA2SO4 and concentrated to dryness. The crude material was distilled under reduced pressure to give 103.8 g (52%) of compound ii. In a flame dried flask under N2 blanket, compound ii (6.0 g, 30.5 MMOL) was dissolved in dry THF (30 mL) and cooled TO-78 C. A solution of n-butyl lithium (1.75 M in hexanes, 17.4 mL, 30.5 MMOL) was added and the reaction mixture was stirred for 20 min. S02 was bubbled in the reaction for 20 min. It was slowly warmed up to rt. CH2CI2 (50 mL) was added and the mixture was reacted with NCS (5.0 g, 37.4 MMOL) at rt overnight. The reaction mixture was washed with brine (100 mL x 2). The organic layer was dried over NA2SO4 and then concentrated to dryness. The crude material was purified via sgc (5% EtOAC/Hexanes) to give 3.65 g (55%) of compound II. To a round-bottom flask was added compound iii (3.0 g, 13.8 MMOL) and KF (2.4 g, 41.4 MMOL) followed by addition of acetone (50 mL) and water (30 mL). The reaction mixture was stirred at room temperature overnight. The solvent was then removed. Methylene chloride (40 mL) was added and it was washed with brine (40 mL). The organic layer was dried over NA2SO4 and then concentrated to dryness to give 2.77 g (100%) of compound E.

The synthetic route of 167404-32-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2004/48322; (2004); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 454-78-4,Some common heterocyclic compound, 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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.

Step 1: To a 500 mL three-neck RBF equipped with a magnetic stirring bar were added, under N2 atmosphere, 3-bromo-4-chloro-benzotrifluoride (16.5 mL, 110 mmol) and dry THF (150 mL). The resulting solution was cooled to 0 C. To this solution was added z’-PrMgBr (110 mL, 110 mmol) and the reaction was warmed to rt and stirred for 1 h. To another 500 mL RBF containing a solution of CuBr Me2S (18.8 g, 91.5 mmol) in THF (100 mL) was added BF3*OEt2 (14 mL, 110 mmol) dropwise at -40 C. The resulting solution was stirred at that temperature for 45 min. Then, the Grignard reagent prepared previously was added dropwise to this solution while maintaining the internal temperature at -32 to -38 C. After completion of addition, the reaction mixture was stirred at that temperature for 1 h. The reaction mixture was cooled to -78 C, and a solution of (2S)-l-t-butyl 2-ethyl 5-methoxypyrrolidine-l ,2- dicarboxylate (25.0 g, 91.5 mmol) in THF (50 mL) was added dropwise. The resulting reaction mixture was allowed to warm up to rt and was stirred for 14 h. The reaction mixture was cooled to 0 C, and saturated aqueous NH4C1 solution (100 mL) was added followed by aqueous NH4OH solution (100 mL) and water (300 mL). The layers were separated. The aqueous layer was extracted with EtOAc (3 x 200 mL). The combined organics were dried over anhydrous Na2S04 and concentrated. The crude product was purified by column chromatography eluting with 5% EtOAc in petroleum ether to yield (2S,5S)-l-tert-butyl 2-ethyl 5-(2-chloro-5- (trifluoromethyl)phenyl)pyrrolidine-l,2-dicarboxylate (34.0 g, 79.8 mmol) as a colorless liquid. 1H NMR (400 MHz, CDC13) 7.32-7.47 (m, 3 H), 5.39-5.50 (m, 1 H), 4.58-4.70 (m, 1 H), 4.22- 4.28 (m, 2 H), 2.55 (m, 1 H), 2.18 (m, 1 H), 2.05 (m, 1 H), 1.83 (m, 1 H), 1.16-1.43 (m, 12 H); LC-MS ESI calc’d. for Ci9H23ClF3N04 [M-Boc]+ 321.84, found 322.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIU, Jian; SHAO, Pengcheng Patrick; KRIKORIAN, Arto, D.; VACHAL, Petr; WO2015/17302; (2015); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 454-78-4, A common heterocyclic compound, 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrClF3, 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.

To a solution of l-bromo-2-chloro -4-(trifluoromethyl)benzene (1.5 mL, 10 mmol) in 30 mL of anhydrous THF was added Pd(PPh3)2Cl2 (351mg, 0.5 mmol), triphenylphosphine (65 mg, 0.25 mmol), ethynyl(trimethyl)silane (2.12 mL, 15 mmol), and triethylamine (2.1 mL, 15 mmol). The reaction was stirred at room temperature for 20 minutes after which CuI (23 mg, 0.12 mmol) was added to the solution and the reaction was stirred at room temperature for 16 hours. The reaction was then concentrated in vacuo and the resulting residue was dissolved in hexanes, filtered through Celite and again concentrated in vacuo. The residue was purified by flash column chromatography using 100% hexanes to afford the desired product as a dark brown oil. 1H NMR (CDCl3, 500MHz: 7.8 (d, 7=1.6 Hz, IH), 7.5 (m, 2H), 0.23 (s, 9H).

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; MERCK & CO., INC.; WO2006/14618; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 454-78-4, 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. 454-78-4, name is 2-Bromo-1-chloro-4-(trifluoromethyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1: tert-Butyl 4-[2-chloro-5-(trifluoromethyl)phenyl]piperazine-1-carboxylate Into a 50 mL pressure vial equipped with a magnetic stir bar was added tert-butyl piperazine-1-carboxylate (2.00 g, 10.7 mmol), palladium(II) acetate (0.24 g, 1.07 mmol) and racemic-BINAP (1.34 g, 2.15 mmol). The vial was evacuated under vacuum (1 mm Hg) and backfilled with N2 (repeated 3 times). Toluene (10 mL) and 3-bromo-4-chlorobenzotrifluoride (3.06 g, 11.8 mmol) were added to the vial and the solvent was degassed for 10 min with a steady flow of nitrogen before being heated to 120 C. for 16 h. The reaction mixture was filtered through a plug of celite on a sintered glass funnel, washing with diethyl ether (100 mL). The filtrate was concentrated and purified by column chromatography through silica gel, eluting with 0% EtOAc in hexanes to 40% EtOAc in hexanes as a gradient. The desired product was obtained as a light yellow oil.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-1-chloro-4-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Isabel, Elise; Lachance, Nicolas; Leclerc, Jean-Philippe; Leger, Serge; Oballa, Renata M.; Powell, David; Ramtohul, Yeeman K.; Roy, Patrick; Tranmer, Geoffrey K.; Aspiotis, Renee; Li, Lianhai; Martins, Evelyn; US2011/301143; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics