Month: September 2021

70558-11-1, name is 6-Chloro-3,4-dihydro-2H-benzo[b][1,4]oxazine, 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. HPLC of Formula: C8H8ClNO

Reference Example 82 Production of (6-chloro-2,3-dihydrobenzo[1,4]oxazin-4-yl)-(3,5-dibromo-4-hydroxyphenyl)-methanone 6-Chloro-3,4-dihydro-2H-benzo[1,4]oxazine (170.6 mg) obtained in Step 3 of Reference Example 51 and 3,5-dibromo-4-hydroxybenzoyl chloride (349.3 mg) obtained in Step 1 of Reference Example 4 were dissolved in ethyl acetate (5 mL), and the mixture was heated under reflux overnight. The solvent was evaporated, and the obtained solid was crystallized from methanol to give the title compound (441.0 mg) as crystals.

The synthetic route of 70558-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Japan Tobacco Inc.; US2008/305169; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2268-05-5, The chemical industry reduces the impact on the environment during synthesis 2268-05-5, name is 2,6-Dichlorofluorobenzene, I believe this compound will play a more active role in future production and life.

4,4,4>,4>,5,5,5′,5′-Octamethyl[2,2′-bi-1,3,2-dioxaborolane] (10.0 g, 39.4 mmol), 2,6- bis(l-methylethyl)-N-(2-pyridinylmethylene)benzenamine (0.40 g, 1.5 mmol), and i-mu- chlorobis[(1,2,5,6- eta)-1,5-cyclooctadiene]diiridium (0.50 g, 1.0 mmol) were added to a solution of 1,3-dichloro-2-fluorobenzene (10.0 g, 60.6 mmol) in heptane (200 mL). The reaction mixture turned from yellow to forest green to brick red within the first minute. The reaction mixture was heated to reflux for 18 h. The mixture was then partitioned between ethyl acetate and water, and the aqueous extract was washed twice with ethyl acetate. The organic extracts were combined, dried over MgSOphi and concentrated under reduced pressure. The solid residue was purified by chromatography on silica gel by elution with ethyl acetate/hexane to afford the title compound as a solid (11.0 g). 1H NMR (CDCl3) delta 7.72 (d, 2H), 1.33 (s, 12H).

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, 2,6-Dichlorofluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WO2009/51956; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 20850-43-5,Some common heterocyclic compound, 20850-43-5, name is 5-(Chloromethyl)benzo[d][1,3]dioxole, molecular formula is C8H7ClO2, 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 slurry of magnesium turnings (1.09 g, 44.8 mmol) in 5 mL of THF was added iodine (0.0650 g, 0.256 mmol), followed by a solution of 5-(chloromethyl)benzo[d][l,3]dioxole (6.55 g, 38.4 mmol) in 30 mL of THF. After 1 minute, the exothermic reaction mixture was placed in an ice bath for 1 minute and then stirred at ambient temperature for 1 hour. TMEDA (7.68 ml, 51.2 mmol) was added to the reaction and the mixture was cooled to -78 0C for 5 minutes at which point a solution of (E)-N-((S)-2,3-bis(tert- butyldimethylsilyloxy)propylidene)-2-methylpropane-2-sulfinamide (5400 mg, 12.8 mmol) in 25 mL THF was added via a syring pump over 15 minutes. The reaction was allowed to warm to RT over the course of 2 hours then stirerd at RT for an additional hour. The mixture was diluted with ethyl acetate (100 mL) and poured in saturated ammonium chloride (250 mL). The aqueous layer was extracted with ethyl acetate (2 x 250 mL) and the combined organic layers were washed with water and then brine and dried over Na2SO4. The organic colvents were filtered, concentrated under reduced pressure and the crude material was purified by silica gel to provide N-((2R,3S)-1- (benzo[d][l,3]dioxol-5-yl)-3,4-bis(tert-butyldimethylsilyloxy)butan-2-yl)-2- methylpropane-2-sulfinamide (4.51 g, 63.1% yield) as a colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Chloromethyl)benzo[d][1,3]dioxole, its application will become more common.

Reference:
Patent; AMGEN INC.; WO2009/64418; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 2613-34-5, 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. 2613-34-5, name is 3-Chloro-2,4-difluoroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2- yl)sulfamoyl)-1H-pyrrole-2-carboxylic acid (450 mg, 1.43 mmol) and 3-chloro-4,5- difluoroaniline hydrochloride (0.57 g, 2.86 mmol) (synthesis described in synthesis for compound 57) and HATU (0.73 g, 1.91 mmol) were dissolved in DMF (2 mL) containingdiisopropylethylamine (0.82 mL, 4.77 mmol). The reaction mixture was stirred at 40C for 66 hours. The reaction mixture was directly loaded on column. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combined and evaporated to keep 50 mL of solvent. The precipitates were filtered and washed with petroleum ether and dried in vacuum oven at 50C overnight to affordcompound 137 (490 mg) as white powder.(R)- 1,5 -dimethyl-4-(N-( 1,1,1 -trifluoropropan-2-yl)sulfamoyl)- 1 H-pyrrole-2-carboxylic acid (168mg, 0.53 mmol) (synthesis described in synthesis for compound 137) 5-amino-2-fluorobenzonitrile (0.15 g, 1.07 mmol) and HATU (0.24 g, 0.64 mmol) were dissolved in DMF (1 mL) containing diisopropylethylamine (0.23 mL, 1.34 mmol). The reaction mixture was stirred at 50C for 1 hour. The reaction mixture was purified using silica gel column chromatography (ethyl acetate in heptane from 20 to 80%). The desired fractions were combinedand evaporated to keep 50 mL of the solvent. The white solids were filtered and dried invacuum oven to afford compound 140 (180 mg) as white powder.Compound 143 (147 mg) as white powder was synthesized similarly as described for compound140 using 3-chloro-2,4-difluoroaniline (0.17 g, 1.07 mmol) instead of 5-amino-2-fluorobenzonitrile. The reaction mixture was stirred at 60C for 2 hours more. Method B; Rt:1.07 mi mlz: 458 (M-H) Exact mass: 459.04. ?H NMR (400 MHz, DMSO-d6) oe ppm 1.09 (d,J7.0 Hz, 3 H), 2.44 (s, 3 H), 3.82 (s, 3 H), 3.76 – 3.91 (m, 1 H), 7.34 (td, J=9.0, 2.0 Hz, 1 H),7.35 (s, 1 H), 7.52 (td, J8.7, 5.8 Hz, 1 H), 8.20 (br. s., 1 H), 10.05 (s, 1 H).

The synthetic route of 3-Chloro-2,4-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 33863-76-2,Some common heterocyclic compound, 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, molecular formula is C6H3BrClF, 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.

Preparation 5 TERT-BUTYL 3-(3-CHLORO-5-FLUOROPHENYL)-3-HYDROXYPYRROLIDIN-1-CARBOXYLATE To a solution of 1-bromo-3-chloro-5-fluorobenzene (4.0 g, 19.1 mmol) in dry tetrahydrofuran (40 mL), under nitrogen, was added magnesium turnings (0.47 g, 21.0 mmol) and a small piece of iodine. The mixture was heated with a heat-gun until the colour disappeared and then stirred at ambient temperature for 0.5 h after which a solution of 1-N-boc-3-pyrrolidinone (2.8 g, 15.3 mmol) in dry tetrahydrofuran (10 mL) was added drop wise. The reaction mixture was stirred for 0.5 h at ambient temperature and then quenched with water (70 mL). Aqueous saturated ammonium chloride (20 mL) was added and the mixture was extracted with ethyl acetate (2*100 mL). The combined organic phase was dried (MgSO4), filtered and evaporated. Purification by flash column chromatography on silica gel (ethyl acetate/isooctane, 1:1) gave the title compound (2.43 g). MS m/z (rel. intensity, 70 eV) 315 (M+, 1), 259 (14), 214 (22), 184 (13), 143 (11), 57 (bp).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3-chloro-5-fluorobenzene, its application will become more common.

Reference:
Patent; NSAB, FILIAL AF NEUROSEARCH SWEDEN AB; US2010/179211; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

60811-21-4,Some common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, molecular formula is C6H3BrClF, 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 dissoprppylamine (5.1 mL, 36.0 mmol, 1.5 eq.) in anhydrous THF (15 mL) was added n-BuLi (19.2 mL, 28.8 mmol, 1.2eq.) dropwise at -78C under N2 atmosphere, then was added the 4-bromo-2-chloro-l-fluorobenzene (5 g, 24.0 mmol, 1.0 eq.) at -78C 1 h later. The mixture was stirred at -78C for 45 minutes, then was added DMF (2.8 mL, 36.0 mmol, 1.5 eq. ), warmed to -30C until TLC showed that the reaction was completed. The reaction was quenched with H20 (100 mL), then adjusted to pH 2-3, extracted with EA (50 mLx3). The combined organic layers were washed with brine, dried over anhydrous Na2S04 and evaporated. The residue was purified by column chromatography (PE/EA=100: 1) to provide 5-bromo-3-chloro-2-fluoroben low solid.

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

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; QIAN, Shawn; (297 pag.)WO2018/229543; (2018); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 72235-58-6,Some common heterocyclic compound, 72235-58-6, name is (4-Chloro-3-fluorophenyl)methanamine, molecular formula is C7H7ClFN, 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 3: Intermediate 201 OB (50 mg, 0.16 mmol) is dissolved in DMF (2.0 ml_), then diisopropylethylamine (1 10 muIota_, 0.63 mmol, 4.0 eq) and 4-chloro-3-fluorobenzylamine ( Oakwood) (30 mg, 0.19 mmol, 1 .2 eq) are added followed by HATU (78 mg, 0.21 mmol, 1 .2 eq) and the reaction mixture is stirred at RT. Following completion of the reaction, the solution is filtered and purified by preparative HPLC to provide compound 2010 (tR: 1 .71 , (M+H)+: 459.2/461 .2).

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-fluorophenyl)methanamine, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; LEPAGE, Olivier; BAILEY, Murray; BEAULIEU, Pierre Louis; BILODEAU, Francois; CARSON, Rebekah; GIROUX, Andre; GODBOUT, Cedrickx; MOREAU, Benoit; NAUD, Julie; PARISIEN, Mathieu; POIRIER, Martin; POIRIER, Maude; SURPRENANT, Simon; THIBEAULT, Carl; WO2013/152063; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 1435-48-9, name is 2,4-Dichloro-1-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. Safety of 2,4-Dichloro-1-fluorobenzene

General procedure: As a typical experiment, the reaction of the 2-halopyridine (1 mmol), fluorobenzene derivative (2.5 mmol) and PivOK (0.154 g, 1.1 mmol) at 150 C during 16 h in DMA (3 mL) in the presence of PdCl(C3H5)(dppb) (12 mg, 0.02 mmol) (see tables or schemes) under argon affords the arylation product after evaporation of the solvent and filtration on silica gel

The synthetic route of 2,4-Dichloro-1-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Boyaala, Rabab; Touzani, Rachid; Guerchais, Veronique; Soule, Jean-Francois; Doucet, Henri; Tetrahedron Letters; vol. 58; 33; (2017); p. 3205 – 3208;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6529-53-9, The chemical industry reduces the impact on the environment during synthesis 6529-53-9, name is 1-(2-Bromoethyl)-4-chlorobenzene, I believe this compound will play a more active role in future production and life.

Example 1.49: Preparation of (4-Chloro-l-methyl-lH-pyrazol-3-yl)-{4-[2-(4- chlorophenyl)-ethyl]-piperazin-l-yl}-methanone (Compound 44). In a heavy-walled sealed tube, (4-chloro-l-methyl-lH-pyrazol-3-yl)(piperazin-l- yl)methanone dihydrochloride (27 mg, 0.10 mmol) was dissolved in DMF (1.0 mL). 4- Chlorophenethyl bromide (12 mg, 0.083 mmol) and potassium carbonate (35 mg, 2.5 mmol) were added. The reaction was heated under microwave irradiation for 10 min at 100 C. The solids were filtered and the filtrate was purified by preparative HPLC. The best fractions were lyophilized to afford the TFA salt of the title compound (15 mg) as a white solid. 1H NMR (DMSO-d6, 400 MHz) delta 2.96-3.03 (m, 2H), 3.03-3.28 (m, 2H), 3.30-3.75 (m, 6H), 3.87 (s 3H), 4.23-4.40 (bs, IH), 4.46-4.65 (bs, IH), 7.32 (d, J = 8.4 Hz, 2H), 7.43 (d, J = 8.3 Hz, 2H), 8.10 (s, IH). Exact mass calculated for Ci7H20Cl2N4O: 366.1; Found: LCMS m/z (%) = 367.4 (M+H+ 35Cl, 100%), 369.4 (M+H+ 37Cl, 64%).

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-(2-Bromoethyl)-4-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2008/42388; (2008); A1;,
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. 766545-20-4, name is 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride, A new synthetic method of this compound is introduced below., Quality Control of 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride

Preparation 26 2-Amino-1-(7w8-dihydro-5H-r1, 61naphthvridin-6-yl)-ethanone; Step A A solution of 90 mg of 2-chloro-5, 6,7, 8-tetrahydro- [1, 6] naphthyridine hydrochloride (U. S. Pat. No. 6,169, 093), 0.134 g of N-carbobenzyloxyglycine, 0.130 g of triethylamine, and 0.087 g of 1-hydroxy-7-azabenzotriazole in DMF (2.7 mL) at 0 C was stirred as 0.123 g (0.640 mmol) of EDC was added. After two h, the reaction mixture was poured into 4% magnesium sulfate solution, and the resulting solution was extracted with EtOAc and then methylene chloride. The organic extracts were dried over sodium sulfate, filtered, and concentrated to give an oil that solidified upon standing. Trituration with MeOH and collection of the solids provided the desired amide intermediate.

The synthetic route of 766545-20-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2005/35532; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics