Month: June 2021

Application of 1996-30-1, 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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

The title compound (150 mg, 12.7 %, off-white solid) was obtained from [4- [1- (5-] tributylstannanyl-isoxazol-3-yl)-ethyl]-piperazine-l-carboxylic acid ethyl ester (1.063 g, 1.98 mmol) and Pd (PPh3) [2C12] (19.2 mg) with [2-BROMO-4-CHLORO-1-FLUORO-BENZENE] (368mg, 1.76 mmol) in dioxane (lOmL) at 110 [C] overnight. 1H-NMR (CDC13) 8 (ppm): 7.94 (dd, 1H), 7.40 (m, 1H), 7.17 (dd, 1H), 6.71 (d, [1H),] 4.13 (q, 2H), 3.90 (q, 1H), 3.51 (m, 4H), 2.52 (m, 4H), 1.86 (d, 3H) and 1.26 (t, 3H).

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-fluorochlorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ASTRAZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14370; (2004); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 6940-78-9, name is 1-Bromo-4-chlorobutane, molecular formula is C4H8BrCl, 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 C4H8BrCl

Example (C):1Preparation of 7-(4-cMorobutoxy)-3,4-dihydro carbostyril (III):; The three necked flask was charged with 7-hydroxy-3, 4-dihydro carbostyril (II) (50gm, 0.306moles) in acetone: water mixture (400ml: 25ml). To this mixture was successively added potassium carbonate (50,8gm, 0,367moles), PEG-400 (61.2gm) and stirred at ambient temperature for one hour. The l-bromo-4-chlorobutane (157ml, 0.918moles) was added to mixture over a period of 10 min. Reaction mixture was then stirred at ambient temperature for 15-16 hours. The progress of the reaction was monitored by TLC (eluent: chloroform: methanol (90:10)). Reaction mixture was filtered and the inorganics were washed with acetone (100ml). The solvent was removed under the reduced pressure below 40 0C. The thick oily residue obtained was stirred with n-hexane (500ml) and water (500ml), at 10-15 0C, for a period of 45 min.The solid was filtered, washed with water (500ml) and then with n-hexane (500ml). The resulting solid was dried at 65-70 0C to obtain 7-(4-chlorobutoxy)-3, 4-dihydro carbostyril (III) (72.7gm, 94 %).1H (CDCl3): 1.9 (m, 4H), 2.5 (m, 2H), 2.8 (m, 2H), 3.6 (m, 2H), 3.9 (m, 2H), 6.3 (s, IH), 6.4 (d, IH), 7.0 (d, IH) and 9.3 (s, IH)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6940-78-9, its application will become more common.

Reference:
Patent; UNICHEM LABORATORIES LIMITED; WO2007/94009; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39065-95-7, A common heterocyclic compound, 39065-95-7, name is 4-(Chlorodifluoromethoxy)aniline, molecular formula is C7H6ClF2NO, 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 mixture of 1,2-dimethyl-4-(pyrimidin-5-yl)-1H-benzo[d]imidazole-6-carboxylic acid (4d, 15 mg, 0.056 mmol, 1 eq) and HATU (25.51 mg, 0.067 mmol, 1.2 eq), DIPEA (14.45 mg, 0.112 mmol, 19.48 uL, 2 eq) in DMF (1 mL) at 20 C. was added 4-[chloro(difluoro)methoxy]aniline (1h, 16.24 mg, 0.084 mmol, 1.5 eq). The mixture was stirred at 20 C. for 16 hours. The mixture was concentrated in vacuo. LCMS showed desired MS. The mixture was poured into water and extracted with EtOAc, and the combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the crude product. The residue was purified by prep-HPLC (TFA condition, column: Nano-Micro UniSil 5-100 C18 ULTRA 100*250 mm 5 um; mobile phase: [water (0.1%TFA)-ACN]; B %: 25%-50%, 11 min) to afford the title compound 4 as a white solid. MS mass calculated for [M+H]+ (C21H16ClF2N5O2) requires m/z 444.1, LCMS found m/z 444.1. 1H NMR (400 MHz, MeOD-d4) delta 9.33-9.25 (m, 3H), 8.48 (s, 1H), 8.25 (s, 1H), 7.88 (d, J=9.0 Hz, 2H), 7.33 (d, J=8.8 Hz, 2H), 4.07 (s, 3H), 2.85 (s, 3H).

The synthetic route of 39065-95-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Terns, Inc.; ROMERO, F. Anthony; KIRSCHBERG, Thorsten A.; HALCOMB, Randall; XU, Yingzi; (144 pag.)US2020/87283; (2020); 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. 2163-00-0, name is 1,6-Dichlorohexane belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: chlorides-buliding-blocks

A 250 mL four-necked flask equipped with a mechanical stirrer, a thermometer and a reflux condenser was used as the reaction vessel. 32. 3 g (0.13 mol) of sodium thiosulfate pentahydrate was weighed out, 70.0 g of water and 35. 0 g of DMF were added, After stirring and dissolving, 9.3 g (0.06 mol) of 1,6-dichlorohexane was added while stirring. The temperature of the solution was raised by heating, and the temperature of the reaction solution was raised to 90 C. The reaction was stirred at this temperature for 6 h, Hexamethylene-1,6-dithiosulfate disodium salt (HTS) solution. The resulting hexamethylene-1,6-dithio-sulfate disodium salt solution was analyzed by a gas chromatograph (GC) and a liquid chromatograph (HPLC), respectively, to measure 1,6-dichlorohexane and thiosulfate Sodium in the solution

The synthetic route of 2163-00-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Red Avenue Innova Co., Ltd; Zhen, Boming; Dong, Dong; Zhao, Lili; fang, Caiqin; Ruan, zhen Gang; Hu, Xiaona; (10 pag.)CN105218419; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 64628-73-5, 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. 64628-73-5 name is 3-Chloro-4-(trifluoromethoxy)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.

A) 3-(3-Chloro-4-trifluoromethoxy-phenylamino)-propionic acid tert-butyl ester A solution of 9.26 g (42.4 mmol) of 3-chloro-4-trifluoromethoxy-phenylamine and 4.39 ml (42.4 mmol) of 2,6-lutidine in 50 ml of toluene was treated slowly with 7.30 ml (42.4 mmol) of tert-butyl 3-bromopropionate and stirred 2 days at reflux temperature. The reaction was then partitioned between aqueous 10% KHSO4 and EtOAc (3*). The organic phases were washed with 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane:EtOAc 9:1) to yield 9.59 g (60%) of the title compound as brown liquid. MS: 339 (M+, Cl).

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

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Green, Luke; Hartmann, Guido; Maerki, Hans P.; Mattei, Patrizio; US2011/92698; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, 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 13918-92-8, Computed Properties of C6H3ClF2O2S

General procedure: A mixture of norfloxacin (a) or ciprofloxacin (b) (1 mmol) (refPreviewPlaceHolderScheme 1) and K2CO3 (152 mg, 1.1 mmol) was stirred in acetone (20 mL) at room temperature for 20 min. To the resulted mixture, the appropriate arenesulfonyl chloride (1.2 mmol) in acetone (5 mL) was added dropwise over a period of 20 min. The reaction mixture was further stirred at room temperature for 24 h. The separated solid was then filtered, washed with cold water, dried and crystallized from the appropriate solvent.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Difluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Abdel-Aziz, Alaa A.-M.; Asiri, Yousif A.; Al-Agamy, Mohamed H.M.; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5487 – 5497;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 56961-77-4, These common heterocyclic compound, 56961-77-4, name is 1-Bromo-2,3-dichlorobenzene, 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.

Intermediate 1:[0114] A well-dried flask was first charged with l-bromo-2,3-dichlorobenzene (4 g, 17.7 mmol) and 1,4-diazepane (2.1 g, 20.9 mmol), which was evacuated and backfilled with N2 through a balloon under gentle warming (40C). Toluene was charged and the mixture was bubbled with N2 for 10 min, then BINAP (318 mg, 0.51 mmol) and Pd2dba3 (156 mg, 0.17 mmol) was added to the mixture, followed by DBU (3.4 mL). The resulting mixture was warmed at 60- 70C while fine powder of tBuONa was added in one portion to start the amination. After the reaction mixture cooled to rt, (Boc)20 (11 g, 51 mmol) solution in DCM was added dropwise to the reaction mixture, then stirred for 3 h at rt. The reaction mixture was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2S04, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc = 10:1) to give tert-butyl 4-(2,3-dichlorophenyl)-l,4-diazepane- 1-carboxylate (intermediate 1) (4.1 g, 70%) as a yellow oil.

Statistics shows that 1-Bromo-2,3-dichlorobenzene is playing an increasingly important role. we look forward to future research findings about 56961-77-4.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; JIN, Jian; ROTH, Bryan; FRYE, Stephen; WO2012/3418; (2012); A2;,
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. 7149-75-9, name is 4-Chloro-3-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Chloro-3-methylaniline

Step 1 (0642) To a mixture of 1-(3-bromo-4-methylphenyl)ethanone (1.51 g), 4-chloro-3-methylphenylamine (1.0 g) and methanol (14 mL) was added decaborane (259 mg), and the mixture was stirred at room temperature for 12 hours. After the mixture was diluted with ethyl acetate, to the resulting mixture was added aminopropyl silica gel powder (5 g). The resulting mixture was filtered and the filtrate was concentrated under reduced pressure to give [1-(3-bromo-4-methylphenyl)ethyl]-(4-chloro-3-methylphenyl)amine (1.99 g).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7149-75-9.

Reference:
Patent; Kissei Pharmaceutical Co., Ltd.; Inoue, Hitoshi; Ohno, Kohsuke; Nakamura, Tetsuya; Ohsawa, Yusuke; (58 pag.)US2016/362368; (2016); 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. 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 15205-11-5

To a stirred mixture of 1-(2-chloro-4-fluorophenyl)methanamine (80 mg, 0.501 mmol, 1 equiv.) and 4-chloro-5-(4-oxopiperidin-1-yl)-2,3-dihydropyridazin-3-one (114.12 mg, 0.501 mmol, 1.00 equiv.) in DMF (5 mL) were added 1-azido-4-nitrobenzene (115.18 mg, 0.702 mmol, 1.4 equiv.) and Zn(OAc)2 (91.98 mg, 0.501 mmol, 1 equiv.) at room temperature. The resulting mixture was stirred for 16 h at 60 degrees C. The reaction was monitored by LCMS.The mixture was allowed to cool down to room temperature. The mixture was purified by reverse phase flash with the following conditions (Column:C18,330 g; Mobile Phase A: Water/0.05% NH4HCO3, Mobile Phase B:ACN; Flow rate:80 mL/min;Gradient: 35%B to 50%B in 15 min; Detector,220nm and 254nm) to afford crude product. The crude product (30 mg) was purified by Prep-HPLC with the following conditions (Column: XBridge Shield RP18 OBD Column, 5um,19*150mm; Mobile Phase A: Water(10MMOL/L NH4HCO3), Mobile Phase B: ACN; Flow rate: 25 mL/min; (1701) Gradient: 5% B to 16% B in 1 min; 254/220 nm; Rt: 7.47 min) to afford 4-chloro-5-[1-[(2- chloro-4-fluorophenyl)methyl]-1H,4H,5H,6H,7H-[1,2,3]triazolo[4,5-c]pyridin-5-yl]-2,3- dihydropyridazin-3-one(8.3mg,4.19%) as a white solid

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 15205-11-5.

Reference:
Patent; GOLDFINCH BIO, INC.; YU, Maolin; DANIELS, Matthew, H.; HARMANGE, Jean-christophe, P.; TIBBITTS, Thomas, T.; LEDEBOER, Mark, W.; WALSH, Liron; MUNDEL, Peter, H.; MALOJCIC, Goran; (860 pag.)WO2019/55966; (2019); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application 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;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics