Author: Jessica.F

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. Product Details of 918538-05-3

69A. Preparation of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine A solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (1.5 g, 5.3 mmol) in i-PrOH (15 mL) was treated with 3-cyclopropyl-1H-pyrazol-5-amine (657 mg, 5.3 mmol) and DIEA (0.92 mL, 5.3 mmol). The reaction was stirred overnight at ambient temperature and then filtered. The filter cake was washed with cold i-PrOH and dried under vacuum to afford 69A as a solid (1.3 g, 90%). HPLC tR=3.301 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm). [M+H]+=275.37. A solution of 2-chloro-N-(3-cyclopropyl-1H-pyrazol-5-yl)pyrrolo[1,2-f][1,2,4]triazin-4-amine (1A) (100 mg, 0.36 mmol) and piperidine-4-carboxamide (467 mg, 3.6 mmol) in NMP (1 mL) was heated in a microwave safe tube (CEM Corporation, 10 mL) at 100 C. for 40 minutes using 300 W continuous power. The reaction was diluted with EtOAc (10 mL) and washed with 10% aqueous LiCl solution (2*10 mL). The organic layers were combined and dried (Na2SO4), filtered and concentrated. The crude product was purified by preparative reversed-phase HPLC to afford the title compound (23 mg, 15%). HPLC tR=2.398 min (YMC S5 Combiscreen ODS 4.6*50 mm, 10-90% aqueous methanol containing 0.2% H3PO4, 4 min gradient, monitored at 254 nm).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 918538-05-3, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 823-57-4,Some common heterocyclic compound, 823-57-4, name is 2-Bromo-5-chloroaniline, molecular formula is C6H5BrClN, 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 B;. A solution of sodium nitrite (0.63 g, 9.2 mmol) and H2O (1.9 mL) was added dropwise at 0¡ã C. to a solution of 2-bromo-5-chlorobenzenamine (1.6 g, 7.7 mmol) in 12N HCl (18.2 mL) and TFA (2.31 mL). The reaction mixture was stirred at 0¡ã C. for 1 h followed by the dropwise addition of a solution of tin(II)chloride (3.1 g, 16.9 mmol) in 12N HCl (4.6 mL) and H2O (0.6 mL) at 0¡ã C. The reaction mixture stirred for 1 5 h at 20¡ã C. and was filtered and placed under vacuum to give 1 -(2-bromo-5-chlorophenyl)hydrazine hydrochloride (2.0 g, 7.8 mmol).

The synthetic route of 823-57-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/27178; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 75717-77-0, 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. 75717-77-0 name is 2,4-Dichlorophenylacetylene, 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.

Weighed 2,4-dichlorobenzyl alkyne compound (81.6mg, 0.5mmol) into the round bottom flask; re-weighed compound 3,4-methylenedioxy-benzyl azide (120mg, 0.68mmol, 1.4eq) into round-bottomed flask; dimethyl sulfoxide (0.2mL); amount of tert-butanol solution (4mL) and H2O (2mL) dropped to the mixture; after five co-catalyst weighed water copper sulfate (390mg); and then said take ascorbic acid sodium salt (290mg). The clarification becomes cloudy, yellow. Was stirred for 5 hours at room temperature, after treatment experiment, ice-water was added with stirring (15mL), the reaction was quenched; (30mL ¡Á 3) and extracted with ethyl acetate; the organic phase was washed with H2O (25mL ¡Á 2), saturated chloride sodium solution (30mL ¡Á 2) and washed; with an appropriate amount, and the organic phase was dried over anhydrous sodium sulfate; filtered andAnd concentrated to a solid, brown, purified by column chromatography [the V (dichloromethane) :V (petroleum ether) = 1: 1] to give a white solid 125.0 mg,Yield 75%

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

Reference:
Patent; Changzhou University; Chen, Xi; Liang, Cuirong; Yang, Qinghong; Ren, Jie; Jin, Guihua; Huang, Qianhui; Xu, Yuanyuan; Hu, Kun; (32 pag.)CN105440020; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 62356-27-8, The chemical industry reduces the impact on the environment during synthesis 62356-27-8, name is 1-Bromo-3-chloro-2-methylbenzene, I believe this compound will play a more active role in future production and life.

(a) Preparation of 2-bromo-6-chlorobenzylbromide 2-bromo-6-chlorotoluene (20.55 g) and N-bromosuccinimide (19.6 g) were stirred together in carbon tetrachloride (100 ml) under reflux for 22 hours exposure to radiation from an infrared lamp. The resulting solution was cooled in ice, filtered and evaporated to yield the title product which was dissolved in petroleum ether (60-80). Part was recrystallized therefrom as pink needles (8.5 g) and part was recovered by evaporation as a dark orange solid (17.7 g) (total yield 26.2 g. 92%).

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-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shell Oil Company; US4259349; (1981); 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. 627-42-9, name is 2-Methoxyethyl chloride, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

Step (i) N-methoxyethyl-N-methylpyrrolidinium chloride, PYR1(2O1)Cl, was synthesized by reacting N-methylpyrrolidine with the appropriate amount of 2-chloroethyl methyl ether. The reagents were firstly dissolved in ethyl acetate and, then, mixed in a reactor. The reaction temperature was set at 70 C forachieving a yield approaching 100% (determined by weighting the obtained precursor after vacuum drying at 100 C overnight) upon 5-6 days heating due to the low kinetics of the reaction (1) [15,17].A white, solid precipitate of PYR1(2O1)Cl was obtained whereas the yellowish liquid phase (e.g., containing impurities generally very soluble in ethyl acetate) was removed by vacuum filtering (paper filter membrane). Finally, the precursor was rinsed 5 times with ethyl acetate.

The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Moreno; Montanino; Carewska; Appetecchi; Jeremias; Passerini; Electrochimica Acta; vol. 99; (2013); p. 108 – 116;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 20850-43-5, 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. 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[[00244]] To a solution of [4- (8-AZA-BICYCLO] [3.2. [1] OCT-3-] ylamino)-6-chloro-1-(2, 2, [2-TRIFLUORO-ETHYL)-LH-QUINAZOLIN-2-] one (149 mg, 0.320 mmol) in DMF (10 mL) was added triethylamine (0.3 mL) and 5-Chloromethyl-benzo [1, 3] dioxole [(0.] 061 mL, 0.480 mmol). The solution was heated to 50 C and stirred for 6 hrs. The reaction was partitioned between ethyl acetate and water and the organic phase was washed an additional 2 x with water and brine, dried over [NA2SO4,] filtered, and concentrated. The crude residue was purified by flash chromatography (gradient elution: [0-20%] MeOH/dichloromethane) to provide 99 mg white solid [(60%). 1H] NMR (300 MHz, CDCl3) 8 ppm 2.10 (m, 4 H), 2.32 (m, 2 H), 3.56 (m, 3 H), 3.77 (s, 2 H), 4.87 (m, 2 H), 5.96 (s, 2 H), 6.77 (d, J = 8.0 Hz, [1] H), 6.83 (m, [1] H), 6.95 (d, J = 8.1 Hz, [1] H), 7.17 (m, 2 H), 7.56 (dd, J = 2.3, 8.9 Hz, [1] H), 7.91 (s, [1] H); MS (ESI [+Q1MS)] m/z 522 [[M+2H] +]

The synthetic route of 5-(Chloromethyl)benzo[d][1,3]dioxole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2003/106452; (2003); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 104-52-9, name is 3-Phenylpropyl 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 104-52-9, name: 3-Phenylpropyl Chloride

15.5 g (0.10 mol) of 3-phenylchloropropane, 4.1 g (0.05 mol) of ethylamine hydrochloride, 0.2 g of tetrabutylammonium bromide and 50 ml of a sodium hydroxide solution (35% to 40%) were placed in a 250 ml flask.Stirring heated to 85-90 C, insulation reaction, TLC tracking.After completion of the reaction, the aqueous layer was extracted three times with ethyl acetate, and the organic layers were combined.Add anhydrous sodium sulfate drying.The filtrate was concentrated under reduced pressure to give 12.4 g of a brownish yellow liquid.Yield: 88%.

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-Phenylpropyl Chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hebei Kaisheng Pharmaceutical Technology co., LTD; ZHAO, KAI; HOU, JIANPING; ZHAO, YAFENG; YUAN, HONGZHONG; ZHAO, XIAOXIAN; JIAN, YONGXUE; (5 pag.)CN103508898; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 461432-23-5,Some common heterocyclic compound, 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, molecular formula is C15H14BrClO, 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.

Method 4) 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene (4.9 g, 15 mmol) and 20 mL of tetrahydrofuran were added to a 50 mL three-necked flask, and the mixture was stirred and cooled to -5 to 0 C.Slowly add isopropylmagnesium chloride Grignard reagent (8 mL, 2 mol/L).The system was stirred at 0 C for 2 h.In another 100mL three-neck bottle,Add (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triacetyl ester (IIa, 4.1 g, 10 mmol) , tetramethylethylenediamine (10wt%),Cobalt dichloride (10 wt%) and 20 mL of 2-methyltetrahydrofuran,The system was cooled to 0 C.Slowly add the Grignard reagent in the previous 50mL bottle and add it in about 30min.After the completion of the system, the system was warmed to 25 to 30 C, and the mixture was stirred for 2 hours. The system was quenched with 1N aqueous hydrochloric acid and the organic phase was extracted with ethyl acetate.concentrate,Column chromatography (PE/EA=3/1),The target product (4.5 g, yield 84%) was obtained.

The synthetic route of 461432-23-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Fangnan Biological Technology Co., Ltd.; Zhang Nian; (6 pag.)CN104059041; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 139512-70-2, 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. 139512-70-2, name is 4-Chloro-5-fluorobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 0.37 g (1 mmol) of compound 2 and 0.16 g (1 mmol) of 4-chloro,5-fluoro-o-phenylenediamine in 4 mL of polyphosphoric acid was stirred at 200 C. for 4 h and poured into 60 mL of dilute NH4OH. It was extracted with three 60 mL portions of ethyl acetate. The combined organic extracts were washed with 60 mL of brine and concentrated. The residue was chromatographed eluting with a gradient of from 2 to 10% methanol (MeOH) in dichloromethane (DCM) plus 1% NH4OH to give 0.06 g of compound 3a and 0.14 g of compound 3b. 3a: Calcd m/z for C26H23BrFN3.H+=478; found m/z=478. 3b: Calcd m/z for C26H22BrClFN3.H+=512; found m/z=512.

The chemical industry reduces the impact on the environment during synthesis 4-Chloro-5-fluorobenzene-1,2-diamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Schering Corporation; US2005/49269; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 27139-97-5, These common heterocyclic compound, 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, 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 stirred solution of 4-bromo-2-chlorotoluene (10.0 g; 48.7 mmol) and benzoyl peroxide (0.51 g; 2.09 mmol) in 80 mL of carbon tetrachloride was added N-bromosuccinimide (43.3 g; 243 mmol), and the resulting mixture was stirred and heated to reflux. After 15 hours, the mixture was cooled to ambient temperature, and the insoluble material was removed by filtration and washed twice with carbon tetrachloride. The filtrate and washings were combined and evaporated. The residue was purified by silica gel chromatography on a Biotage 65M column, eluting with hexanes to give 17.4 g of 2-bromo-4-chloro-l- (dibromomethyl)benzene as a colorless liquid.

Statistics shows that 2-Bromo-4-chloro-1-methylbenzene is playing an increasingly important role. we look forward to future research findings about 27139-97-5.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2009/158426; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics