Category: chlorides-buliding-blocks

Electric Literature of 2770-01-6, A common heterocyclic compound, 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, molecular formula is C6H4ClN3, 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.

Step A Preparation of 3-[4-(1-carbomethoxy-1-(3,4-methylenedioxy-phenyl)methoxy)-3,5-dipropylphenylmethyl]-4-chloro-3H-imidazo[4,5-c]pyridine Cesium carbonate (117.3 mg, 0.36 mmol) was added to 4-chloroimidazo[4,5-c]pyridine (25 mg, 0.18 mmol) in DMF (2 mL) at room temperature under nitrogen. After stirring for 15 min, a solution of 4-(1-carbomethoxy- 1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dipropylbenzyl bromide (106.5 mg, 0.23 mmol) in DMF (2 mL) was added and the mixture stirred at room temperature for 12 h. The mixture was poured onto ice/water and the crude product that precipitated was collected by filtration. The crude material was pre-adsorbed on silica gel and chromatographed (0 to 50% hexane/ethyl acetate) to afford the title compound (25 mg). 1 H-NMR (CDCl3): delta 8.24 (d, 1H), 8.00 (s, 1H), 7.68 (d, 1H), 7.04 (s, 1H), 6.88 (d, 1H), 6.82 (s, 2H), 6.75 (d, 1H), 5.96 (s, 2H), 5.60 (s,2H), 5.00 (s, 1H), 3.71 (s,3H), 2.35 (m, 4H), 1.40 (m, 4H), 0.78 (t, 6H).

The synthetic route of 2770-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5334598; (1994); A;,
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Application of 2770-01-6, 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. 2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The chiral cyclopentenyl moiety 5 (below) was prepared from D-ribose in 8 steps following a previously reported synthetic method via a chiral induction, a regioselective protection of hydroxy group and ring-closing metathesis with 0.1 mole% of the 2nd generation Grubbs catalyst as key steps. 10; The other key intermediate 7 was synthesized according to the previously reported procedure11 from commercially available 4-amino-2-chloropyridine (6) in 4 steps (overall 54% yield) as shown in Scheme 1. Mitsunobu reaction of 7 with 5 provided a mixture of the N9- and N7-regioisomers (8:9 = 2:1) in 94% yield. The separation of the desired product (8) from the reaction mixture was difficult by silica gel column [isolated yields: 20% (8) and 20% (9), respectively]. The ratio of the two isomers was determined by 1H-NMR, and their configuration was identified by Nuclear Overhouser Effect (ID-NOE), which indicated the interaction between the C1 ‘-H and the aromatic C3-H of compound 8, whereas the same effect was not present in compound 9.

The synthetic route of 4-Chloro-1H-imidazo[4,5-c]pyridine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF GEORGIA RESEARCH FOUNDATION, INC.; WO2007/47793; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 622-24-2, name is (2-Chloroethyl)benzene, molecular formula is C8H9Cl, 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: (2-Chloroethyl)benzene

General procedure: One of 4a-d (1 equiv.) and K2CO3 (3 equiv.) in DMF was stirred at 90C for 1h, then the solution was allowed to cool to 60C and was added different substituted benzyl chlorides or phenyl ethyl chlorides (3 equiv.). The reaction mixture was stirred at 60C for another 7h and allowed to cool to room temperature. The saturated NH4Cl solution was added to quench the reaction. The mixture was diluted with water and extracted with ethyl acetate to afford the crude product that was purified by flash column chromatography on silica gel to yield the target products.4.1.5.1 3-Phenethylbenzo[d]oxazol-2(3H)-one (7a) [39] (0039) White solid. Yield 86%. Mp 116-118C. 1H NMR (300MHz, Chloroform-d): delta(ppm) 7.29 (d, J=7.7Hz, 3H), 7.20 (s, 3H), 7.10 (t, J=5.9Hz, 2H), 6.79 (d, J=7.1Hz, 1H), 4.06 (t, J=7.4Hz, 2H), 3.08 (t, J=7.2Hz, 2H). MS (EI): m/z 240.3 [M+H]+. IR (KBr): 3061, 1767, 1614, 1489, 1258cm-1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 622-24-2, its application will become more common.

Reference:
Article; Zou, Yi; Wang, Yan; Wang, Fang; Luo, Minghao; Li, Yuezhen; Liu, Wen; Huang, Zhangjian; Zhang, Yihua; Guo, Wenjie; Xu, Qiang; Lai, Yisheng; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 199 – 211;,
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Application of 202197-26-0, 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. 202197-26-0 name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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.

General procedure: Followed we described previously, substituted aniline (3.3 mol). The reaction mixture was heated to 130 and stirred for 15 min. The reaction mixture was then cooled to 25 . The acetic acid was evaporated. The reaction mixture was quenched in ice-water (25.0 mL), and adjusted pH~9 with ammonia solution. The mixture was stirred for 0.5 h. The precipitated product was filtered, and the filter cake was washed with water (3 × 10 mL) to afford crude product. The crude product was chromatographed by silica gel, eluting with EtOAc/PE (1:4) to afford residue 13a-13c as white solid (yield 84.3% ~ 92.5%). 1.2.1.1 4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)-6-iodoquinazoline (13a) White power, yield: 92.5%.

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

Reference:
Article; Zhang, Yaling; Gao, Hongliang; Liu, Renjie; Liu, Juan; Chen, Li; Li, Xiabing; Zhao, Lijun; Wang, Wei; Li, Baolin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 18; (2017); p. 4309 – 4313;,
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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. 2106-04-9, name is 3-Chloro-2-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Chloro-2-fluoroaniline

4. 0M HCI in Dioxane (4.0 ml) was added to a stirred suspension of 7- (benzyloxy)-4- chloro-6-methoxyquinazoline (CAS Registry NOL62364-72-9, prepared as described in W098/13354, Example 1) (60 g, 0.2 mol) and 3-CHLORO-2-FLUOROANILINE (31.96 g, 0.22 mol) in acetonitrile (1200 ml). The reaction mixture was heated at 80C for 1 hour then left to stand overnight. Acetonitrile (500 ml) was added and the resulting precipitate filtered, washed with acetonitrile (3 x 500 ml) and dried under vacuum to give 7- (BENZYLOXY)-N- (3-CHLORO-2- fluorophenyl) -6-methoxyquinazolin-4-amine hydrochloride as a beige solid (85.45 g, 96%);

According to the analysis of related databases, 2106-04-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2005/26150; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 367-22-6,Some common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, molecular formula is C6H5ClFN, 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: A solution of the corresponding 1H-indazole-5-carbaldehyde(2), 1-methyl-1H-indazole-5-carbaldehyde (9) or 1-(2-methoxyethyl)-1H-indazole-5-carbaldehyde (10) (1.0 equiv.),different substituted anilines 3e6 (1.1 equiv.) and acetic acid(0.1 mL/mmol, pH 4e5) in ethanol (3.0 mL/mmol) was stirred underreflux until a precipitation took place. After cooling to roomtemperature, the reaction mixture was sonificated until completeprecipitation. The precipitate formed was filtered and dried at70 C. The crude product was purified by column chromatographyon silica gel (mobile phase: dichloromethane/MeOH 9/1 v/v) andrecrystallized three times from petroleum ether/dichloromethane.

The synthetic route of 367-22-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tzvetkov, Nikolay T.; Stammler, Hans-Georg; Georgieva, Maya G.; Russo, Daniela; Faraone, Immacolata; Balacheva, Aneliya A.; Hristova, Silvia; Atanasov, Atanas G.; Milella, Luigi; Antonov, Liudmil; Gastreich, Marcus; European Journal of Medicinal Chemistry; vol. 179; (2019); p. 404 – 422;,
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Chlorides – an overview | ScienceDirect Topics

Related Products of 174913-12-3, The chemical industry reduces the impact on the environment during synthesis 174913-12-3, name is 1-Bromo-3-chloro-5-methoxybenzene, I believe this compound will play a more active role in future production and life.

Step a: A solution of l-bromo-3-chloro-5-methoxybenzene (835 mg, 3.77 mmol), and l,3,5-trichloro-l,3,5-triazinane-2,4,6-trione (299 mg, 1.29 mmol) in DMF (18 mL) was stirred 16 h under N2 and 50 C. After cooling to RT, the reaction mixture was diluted with aqueous NH4C1 and extracted with Et20. The combined organic phases were dried over MgS04, filtered, concentrated, and the resulting residue was purified by silica chromatography (0 to 25% gradient of EtO Ac/heptane) to l-bromo-2,3-dichloro-5-methoxybenzene (720 mg, 2.81 mmol). 1H NMR (400 MHz, CHLOROFORM-^ delta ppm 7.14 (d, J=2.76 Hz, 1 H), 7.01 (d, J=3.01 Hz, 1 H), 3.81 (s, 3 H).

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, 1-Bromo-3-chloro-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; CHEN, Zhuoliang; DORE, Michael; FORTANET, Jorge Garcia; KARKI, Rajesh; KATO, Mitsunori; LAMARCHE, Matthew J.; PEREZ, Lawrence Blas; WILLIAMS, Sarah; SENDZIK, Martin; WO2015/107494; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 210532-25-5, 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. 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 25 mL round bottom flask was added 0.10 g (0.37 mmol, 1.0 eq) of solid JD 1001-002-9, THF 3.2 mL under nitrogen atmosphere.DMAP 0.14 g (1.11 mmol, 3.0 eq), 3,5-difluorobenzenesulfonyl chloride 0.24 g (1.11 mmol, 3.0 eq),The reaction was stirred at room temperature for 3 hours, and the reaction was completed by TLC (developing solvent: PE: EA = 1:1). The reaction was quenched with saturated aqueous NaHCO3 and extracted with ethyl acetate. The organic phase was washed with 0.5N aqueous hydrochloric acid. 2 times, dried anhydrous sodium sulfate, filtered, concentrated organic phase to obtain a solid, separated and purified by high pressure liquid phase (CH3CN:H2O=60:40), lyophilized to obtain about 24mg of product JD1001-2054, the yield is 16% .

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, 3,5-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kunming Jida Pharmaceutical Co., Ltd.; Xiao Xuzhi; Zhang Poyong; Lu Faguan; Wang Zhipeng; Chen Mengran; Guo Kun; Zhou Rui; Zhang Yun; (28 pag.)CN109593061; (2019); A;,
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Chlorides – an overview | ScienceDirect Topics

Reference of 1435-50-3, 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. 1435-50-3, name is 2-Bromo-1,4-dichlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Compound 4 – (4 – (1 – (phenyl-sulfonyl) -3 – vinyl – 1H – pyrrolo [2, 3 – b] pyridine -5 – yl) – 1H – pyrazole -1 – yl) piperidine -1 – carboxylic acid tert-butyl ester (205 mg, 0 . 95 mmol), 2 – bromo – 1, 4 – dichlorobenzene (500 mg, 0.9 mmol), Pd (OAc)2 (4 Mg, 0 . 018 mmol), PPh3 (9 Mg, 0 . 036 mmol), K2 CO3 (310 Mg, 2 . 25 mmol), TBAI (0.09 mmol, 33 mg) and anhydrous DMF (5 ml) the mixture under microwave conditions, for 170 C stirring reaction for 1 hour, cooled to the room temperature, the reaction liquid water (15 ml) washing, using EtOAc (10 mLx 3) extraction, the combined organic phase for salt water (30 ml) washing, anhydrous Na2 SO4 Drying, concentrated under reduced pressure, the residue by silica gel column chromatography (PE/EtOAc (v/v)=1/1) to obtain the title compound as a yellow solid (160 mg, 32%).

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-1,4-dichlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; (88 pag.)CN104119331; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 694-80-4 as follows. category: chlorides-buliding-blocks

General procedure: Step 1: The substituted bromobenzene (1 equiv) and (3-formylphenyl)boronic acid or (4-formylphenyl) boronic acid (1 equiv) were dissolved in a mixture of 1M sodium carbonate aqueous solution (15mL), EtOH (5mL) and toluene (15mL). After nitrogen substitution, Pd(PPh3)4 (0.05 equiv) was added. The reaction mixture was stirred at 80C under nitrogen atmosphere for 12h. The reaction mixture was cooled, and water (15mL) was added. The mixture was diluted with AcOEt (15mL), and the insoluble material was filtered off through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (10:1, v/v) as eluent to afford the desired product 2a-r, 5a and 5b as a solid. Step 2: To a solution of 2a-r, 5a or 5b (1 equiv) in MeOH (10mL) and THF (20mL) was added portionwise sodium borohydride (3 equiv) at 0C and the mixture was stirred at 0C for 1h. The reaction mixture was pouring into ice water (10mL), and extracted with ethyl acetate (3×15mL), the organic fractions were combined, washed with saturated brine (2×15mL) prior to drying over anhydrous sodium sulfate. After filtration and concentrate using a rotary evaporator, the residue was used in next step without further purification. To a solution of the obtained solid (1 equiv) in dichloromethane (20mL) was slowly added thionyl chloride (6 equiv) and a catalytic amount of DMF at room temperature. After stirring at 40C for 4h, the reaction was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (20:1, v/v) as eluent to afford the desired product.

According to the analysis of related databases, 694-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Zheng; Liu, Chunxia; Xu, Xue; Qiu, Qianqian; Su, Xin; Dai, Yuxuan; Yang, Jianyong; Li, Huilan; Shi, Wei; Liao, Chen; Pan, Miaobo; Huang, Wenlong; Qian, Hai; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 458 – 479;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics