Month: September 2021

Application 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

Adding a certain compound to certain chemical reactions, such as: 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, 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 33863-76-2, Safety of 1-Bromo-3-chloro-5-fluorobenzene

Preparation 32 1-Bromo-3-chloro-5-methoxybenzene Sodium methoxide (2.20 ml of a 4.5M solution in methanol, 10.0 mmol) was added dropwise to a stirred solution of 1-fluoro-3-chloro-5-bromobenzene (1.00 g, 4.77 mmol) in methanol (28 ml) at room temperature under nitrogen. The reaction was heated under reflux for 3 days and cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting yellow oil was dissolved in dichloromethane (30 ml). The resulting solution was washed with water (2*20 ml) dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel eluding with cyclohexane to provide the title compound (302 mg) as a colourless oil. 1H-NMR (400 MHz, CDCl3): delta=3.77 (s, 3H), 6.82 (s, 1H), 6.94 (s, 1H), 7.09 (s, 1H). Microanalysis: Found: C, 37.94; H, 2.75. C7H6BrClO requires C, 37.96; H, 2.73%.

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

Reference:
Patent; Jones, Lyn Howard; Mowbray, Charles Eric; Price, David Anthony; Selby, Matthew Duncan; Stupple, Paul Anthony; US2003/100554; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 883499-24-9, name is 1-Bromo-2-chloro-3-fluorobenzene, 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. HPLC of Formula: C6H3BrClF

In a nitrogen atmosphere, a flask containing 1-bromo-2-chloro-3-fluorobenzene (10.2 g, 49 mmol, 1 eq.), 1OH3NP14(m) (23.8 g, 1 eq.), potassium carbonate (13.4 g, 2 eq.), and NMP (70 ml) was heated and stirred at 180 C. After completion of the reaction, the reaction liquid was cooled to room temperature, and NMP was distilled off under reduced pressure. Subsequently, water and toluene were added thereto, and the mixture was partitioned. Subsequently, purification was performed by silica gel column chromatography to obtain ?1Br2CL3Px (3NP14(m))?

The synthetic route of 1-Bromo-2-chloro-3-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kwansei Gakuin Educational Foundation; JNC Corporation; HATAKEYAMA, Takuji; KONDO, Yasuhiro; NAKAMOTO, Keiichi; YANAI, Motoki; (190 pag.)US2018/94000; (2018); 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. 1205-71-6, name is 4-Chloro-N-phenylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C12H10ClN

In a 250 ml round bottom flask, 7-bromobenzo [b] naphtho [2,1-d] furan (12 mmol), copper iodide (15 mmol), potassium tert-butoxide (65 mmol), 1,2-di Aminocyclohexane (12 mmol) and (12 mmol) (4-chloro-phenyl) -phenylamine were added to dry 1,4-dioxane (100 ml) and refluxed for 48 hours under N2 atmosphere. The intermediate was cooled to room temperature, added to water, and then filtered through a pad of celite while extracting with dichloromethane, then washed with water, and dried over anhydrous magnesium sulfate. After filtration and evaporation, the crude product was purified by silica gel column chromatography to obtain Intermediate product HT012-1.

According to the analysis of related databases, 1205-71-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shanghai Tianma Organic Shine Display Co., Ltd.; Zhang Lei; Gao Wei; Niu Jinghua; Dai Wenpeng; Xiao Wenjing; Lu Yan; Zhu Hongyan; (28 pag.)CN110746391; (2020); A;,
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, SDS of cas: 13918-92-8

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., name: 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

Related Products 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.

Step C(2S)(M)-[7-[(4-c loro-3-fluorop enyl)amino]-4-(8-fluoro-5-m2-methyl-1 -oxo-1 ,2-dihyd -3-isoquinolinyl][( 1, 1-dimethylethyl)oxy]ethanoic acid[00186] A degassed mixture of (S)(M)-me y 2-(7-bromo-4-(8-fluoro-5-methylchroman-6- yl)-2-methyl-1-oxo-1 ,2-dihydroisoquinolin-3-yl)-2-(tert-butoxy)acetate (22.00 mg, 0.040 mmol), 4-chloro-3-fluoroaniline (1 1.72 mg, 0.081 mmol) and sodium tert-butoxide (1 1 .61 mg, 0.121 mmol) in 1 ,4-Dioxane (1.0 mL) was treated with Pd2(dba)3 (2.084 mg, 2.013 muetaetaomicronIota) and 2- dicyclohexylphosphino-2′-(N,N-dimethyl-amino)biphenyl (3.17 mg, 8.05 mumol) and then irradiated in the microwave at 100 C for 10 minutes. The mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate, followed by brine. The organic phase was dried over sodium sulfate, filtered and concentrated. The crude residue in methanol (1 .0 mL), tetrahydrofuran (THF) (1 .0 mL) and water (0.2 mL) was treated with lithium hydroxide (19.28 mg, 0.805 mmol) and then heated at 65 C for 4 hours. The mixture was concentrated, water was added and the mixture was adjusted to pH 3 with 1 N hydrochloric acid. The mixture was extracted with ethyl acetate and the extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by reverse phase chromatography to afford the title compound as a tan solid (1 1.8 mg, 49%). 1H NMR (400MHz ,CHLOROFORM-d) delta = 8.10 (m, 1 H), 7.32 – 7.17 (m, 2 H), 6.93 (m, 1 H), 6.89 – 6.74 (m, 3 H), 5.18 (s, 1 H), 4.31 (m, 2 H), 3.71 (s, 3 H), 2.78 – 2.67 (m, 2 H), 2.15 (m, 2 H), 1 .96 (s, 3 H), 1.23 (s, 9 H); LC/MS (m/z) ES+ = 598 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Chloro-3-fluoroaniline, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE LLC; DE LA ROSA, Martha Alicia; HAYDAR, Simon, N.; JOHNS, Brian Alvin; VELTHUISEN, Emile Johann; WO2012/102985; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 33050-38-3, The chemical industry reduces the impact on the environment during synthesis 33050-38-3, name is 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, I believe this compound will play a more active role in future production and life.

b) The 3-chloro-6-(cyclohexyloxy)[1,2,4]triazolo[4,3-b]pyridazine can be prepared in the following way:106 mg of sodium hydride at 60% in oil are added to a solution of 530 mg of cyclohexanol in 5 cm3 of tetrahydrofuran at 0 C. under argon. After stirring for 15 min, 500 mg of 3,6-dichloro[1,2,4]triazolo[4,3-b]pyridazine (commercial) are added. The brown suspension is stirred, allowing the temperature to return gradually to 20 C. for 24 1H). The reaction medium is poured into water and the mixture is extracted with ethyl acetate. After concentration to dryness under vacuum, a brown powder is obtained, which is washed with ether. The filtrate is concentrated to dryness and the oily yellow residue is chromatographed on Biotage Quad 12/25 (KP-SIL, 60 ; 32-63 mum), elution being carried out with a gradient of 100% dichloromethane to 95:5 dichloromethane/methanol. 184 mg of 3-chloro-6-(cyclohexyloxy)[1,2,4]triazolo[4,3-b]pyridazine are thus obtained in the form of a white powder, the characteristics of which are as follows:MASS SPECTRUM: LC/MS Electrospray on WATERS UPLC-SQD:MH+=253+1H NMR SPECTRUM (400 MHz, d6-DMSO) delta ppm: 0.84-1.01 (m, 4H) 1.98 (m, 1H) 7.43 (tdd, J=8.5, 2.6, 1.0 Hz, 1H) 7.51-7.65 (m, 2H) 7.70 (d, J=8.5 Hz, 1H) 7.77 (ddd, J=10.4, 2.6, 1.7 Hz, 1H) 7.88 (ddd, J=7.8, 1.7, 1.0 Hz, 1H) 8.05 (d, J=9.8 Hz, 1H) 8.22 (broad d, J=2.0 Hz, 1H) 8.54 (d, J=9.8 Hz, 1H) 12.68 (broad m, 1H)

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, 3,6-Dichloro-[1,2,4]triazolo[4,3-b]pyridazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; sanofi-aventis; US2010/298315; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1716-42-3, A common heterocyclic compound, 1716-42-3, name is 1-(3-Chloropropoxy)-4-fluorobenzene, molecular formula is C9H10ClFO, 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.

Example B13; A mixture of l-(3-chloropropoxy)-4-fluoro- benzene (0.025 mol), compound 23 (0.02 mol) and sodium carbonate (0.06 mol) in DMF (150ml) was stirred at 60°C for 12h. The mixture was cooled, poured into ice water, acidified with HC1 and neutralized with NH3. The precipitate was filtered off and crystallized from MeOH. The precipitate was filtered off and dried at 60°C. The residue (2.1g) was converted into the hydrochloric acid salt (1:1) in 2-propanol. The precipitate was filtered off and washed with 2-propanol and DIPE. The residue was dried at room temperature, yielding 1.2g (14.4percent) of compound 13, melting point 227.6°C.

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; JANSSEN PHARMACEUTICA N.V.; WO2006/3147; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics