Category: 113118-82-4

Synthetic Route of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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.

NaH (570 mg, 14.24 mmol) was added portion wise to stirred anhydrous DMSO (10 ml_). The mixture was heated to 80C until evolution of gas ceased and then cooled to 0C. A solution of (carbethoxymethyl)- triphenylphosphonium bromide (3.05 g, 7.12 mmol) in DMSO (10 ml_) was then added and the mixture stirred at r.t for 30 min. The mixture was cooled to 0C and a solution of 5-chloronicotinaldehyde (1 .0 g, 7.12 mmol) in DMSO (10 ml_) was added and the mixture was stirred at r.t for 1 h. The mixture was then poured into aqueous 1 M HCI and extracted into DCM (3 x 50 ml_). The organics were combined and washed with H2O (3 x 100 ml_) and brine (3 x 100 ml_), separated, dried (MgSO ) and concentrated. Purification by flash silica column chromatography (gradient elution /’-hex to 25% EtOAc in /-hex) gave the title compound as a yellow solid (1 .1 g, 57%). LCMS (ES+) 271 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; LUCKHURST, Christopher A.; HAUGHAN, Alan F.; BRECCIA, Perla; STOTT, Andrew J.; BURLI, Roland W.; HUGHES, Samantha J.; MUNOZ-SANJUAN, Ignacio; DOMINGUEZ, Celia; MANGETTE, John E.; WO2012/103008; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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.

NaH (570 mg, 14.24 mmol) was added portion wise to stirred anhydrous DMSO (10 ml_). The mixture was heated to 80C until evolution of gas ceased and then cooled to 0C. A solution of (carbethoxymethyl)- triphenylphosphonium bromide (3.05 g, 7.12 mmol) in DMSO (10 ml_) was then added and the mixture stirred at r.t for 30 min. The mixture was cooled to 0C and a solution of 5-chloronicotinaldehyde (1 .0 g, 7.12 mmol) in DMSO (10 ml_) was added and the mixture was stirred at r.t for 1 h. The mixture was then poured into aqueous 1 M HCI and extracted into DCM (3 x 50 ml_). The organics were combined and washed with H2O (3 x 100 ml_) and brine (3 x 100 ml_), separated, dried (MgSO ) and concentrated. Purification by flash silica column chromatography (gradient elution /’-hex to 25% EtOAc in /-hex) gave the title compound as a yellow solid (1 .1 g, 57%). LCMS (ES+) 271 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Patent; CHDI FOUNDATION, INC.; LUCKHURST, Christopher A.; HAUGHAN, Alan F.; BRECCIA, Perla; STOTT, Andrew J.; BURLI, Roland W.; HUGHES, Samantha J.; MUNOZ-SANJUAN, Ignacio; DOMINGUEZ, Celia; MANGETTE, John E.; WO2012/103008; (2012); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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.

General procedure: To each reaction tube in a 24-position Bohdan MiniBlock XT was added the appropriate aldehyde (5.0 equiv, 1.15 mmol), which was dissolved in MeCN (1 mL). A solution of 2-(benzo[d][1,3]dioxol-5- yl)pyrimidin-4-amine (8) in MeCN (0.13 M, 1.8 mL, 0.23 mmol, 1.0 equiv) was then dispensed into each tube. ClTi(Oi-Pr)3 (95%, 0.35 mL, 1.38 mmol, 6.0 equiv) was added to each tube, followed by AcOH (3 drops). The reactions were shaken at 450 rpm for 5 minutes, and then solid NaBH(OAc)3 (95%, 257 mg, 1.15 mmol, 5.0 equiv) was added to each tube. The reactions were shaken at 450 rpm for an additional 1.5 hours, and then a solution of 15% aqueous NH4OH (2 mL) and CH2Cl2 (2 mL) were added to each tube causing white solids to precipitate. Shaking was continued for 30 minutes at 450 rpm. Using stackable 24-position Bohdan MiniBlock XTs, the liquid portions of the crude reaction mixtures were passed into phase separators, to which H2O (2 mL) was added. The biphasic mixtures were mixed by hand using pipettes, and then the heavier organic layers were passed from the phase separators into new reaction tubes. The white solids in the original reaction tubes were washed with CH2Cl2 (2 mL) and the washings were passed into the closed phase separators. The biphasic mixtures were again mixed by hand using pipettes and the heavier organic layers were passed into the reaction tubes containing the organic layers from the first separation. The crude reaction mixtures were then placed on a sample concentrator to remove the solvents. TFA/MeOH (1:19, 3 mL) was added to each crude reaction mixture, and the samples were then shaken at 450 rpm for 1 hour. The solutions were then passed onto columns of Dowex 50WX4-400 ion exchange resin (2.0 g, pre-washed with TFA/MeOH (1:99, 5 mL)). Each reaction tube was washed with MeOH (2 mL) and the washings were allowed to pass onto the Dowex columns. The columns were washed with MeOH (3 mL) and the washings discarded. The products were then eluted into collection tubes using a mixture of Et3N/MeOH (1:9, 10 mL). Solvents were removed using a sample concentrator and the products were subjected to reverse-phase preparative HPLC purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Article; Coombs, Thomas C.; Tanega, Cordelle; Shen, Min; Wang, Jenna L.; Auld, Douglas S.; Gerritz, Samuel W.; Schoenen, Frank J.; Thomas, Craig J.; Aube, Jeffrey; Bioorganic and Medicinal Chemistry Letters; vol. 23; 12; (2013); p. 3654 – 3661;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 113118-82-4 ,Some common heterocyclic compound, 113118-82-4, molecular formula is C6H4ClNO, 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.

General procedure: To each reaction tube in a 24-position Bohdan MiniBlock XT was added the appropriate aldehyde (5.0 equiv, 1.15 mmol), which was dissolved in MeCN (1 mL). A solution of 2-(benzo[d][1,3]dioxol-5- yl)pyrimidin-4-amine (8) in MeCN (0.13 M, 1.8 mL, 0.23 mmol, 1.0 equiv) was then dispensed into each tube. ClTi(Oi-Pr)3 (95%, 0.35 mL, 1.38 mmol, 6.0 equiv) was added to each tube, followed by AcOH (3 drops). The reactions were shaken at 450 rpm for 5 minutes, and then solid NaBH(OAc)3 (95%, 257 mg, 1.15 mmol, 5.0 equiv) was added to each tube. The reactions were shaken at 450 rpm for an additional 1.5 hours, and then a solution of 15% aqueous NH4OH (2 mL) and CH2Cl2 (2 mL) were added to each tube causing white solids to precipitate. Shaking was continued for 30 minutes at 450 rpm. Using stackable 24-position Bohdan MiniBlock XTs, the liquid portions of the crude reaction mixtures were passed into phase separators, to which H2O (2 mL) was added. The biphasic mixtures were mixed by hand using pipettes, and then the heavier organic layers were passed from the phase separators into new reaction tubes. The white solids in the original reaction tubes were washed with CH2Cl2 (2 mL) and the washings were passed into the closed phase separators. The biphasic mixtures were again mixed by hand using pipettes and the heavier organic layers were passed into the reaction tubes containing the organic layers from the first separation. The crude reaction mixtures were then placed on a sample concentrator to remove the solvents. TFA/MeOH (1:19, 3 mL) was added to each crude reaction mixture, and the samples were then shaken at 450 rpm for 1 hour. The solutions were then passed onto columns of Dowex 50WX4-400 ion exchange resin (2.0 g, pre-washed with TFA/MeOH (1:99, 5 mL)). Each reaction tube was washed with MeOH (2 mL) and the washings were allowed to pass onto the Dowex columns. The columns were washed with MeOH (3 mL) and the washings discarded. The products were then eluted into collection tubes using a mixture of Et3N/MeOH (1:9, 10 mL). Solvents were removed using a sample concentrator and the products were subjected to reverse-phase preparative HPLC purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,113118-82-4, its application will become more common.

Reference:
Article; Coombs, Thomas C.; Tanega, Cordelle; Shen, Min; Wang, Jenna L.; Auld, Douglas S.; Gerritz, Samuel W.; Schoenen, Frank J.; Thomas, Craig J.; Aube, Jeffrey; Bioorganic and Medicinal Chemistry Letters; vol. 23; 12; (2013); p. 3654 – 3661;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 113118-82-4, name is 5-Chloronicotinaldehyde. A new synthetic method of this compound is introduced below., Formula: C6H4ClNO

3-Chloro-5-formylpyridine (0.50 g, 3.57 mmol), ethylcyanoacetate (0.40 g, 3.57 ramol), N- cyclopropylguanidine.HCl (0.48 g, 3.57 mmol), and potassium carbonate (0.54 g, 3.92 mmol) was stirred in ethanol (20 mL) at 75 0C for 18 hours. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated and concentrated to give a residue which was purified using flash chromatography (100% EtOAc) to give 5-cyano-4-(3- chloro-5-pyridyl)-2-cydopropylamino-6-oxopyrimidine (0.26 g, 26%). MS m/z calculated for (M + H)+ 287, found 287.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 113118-82-4, 5-Chloronicotinaldehyde.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde, molecular formula is C6H4ClNO, The 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.

5.1.96 EXAMPLE 96: SYNTHESIS OF 2-(5-CHLOROPYRIDIN- 3-YL)-8-OXO-9-(2-(TRIFLUOROMETHYL)PHENYL)-8,9-DIHYDRO-7H-PURINE-6-CARBOXAMIDE; EPO [00432] A. Z-CS-Chloropyridin-S-yO-S-oxo^-CZ^trifluoromethyOphenyO-S^- dihydro-7H-purine-6-carboxamide. (Z)-l-(2-Amino-l ,2-dicyanovinyl)-3-(2- (trifluoromethyl)phenyl)urea {See Example 50.A) (0.15 g, 0.51 mmol), 5- chloronicotinaldehyde (0.14 g, 0.99 mmol), and triethylamine (0.10 ml, 0.72 mmol) were combined in methanol (7.0 mL) and stirred at room temperature overnight. Excess solvent was removed under reduced pressure and the resulting residue was purified by reverse-phase preparatory HPLC (30-80% acetonitrile + 0.1% TFA in H2O + 0.1% TFA, over 30 min). Clean fractions were neutralized with ammonium hydroxide and solvent removed under reduced pressure. The resulting material was taken up in ethyl acetate, washed successively with potassium carbonate, water, and brine. The solution was dried over sodium sulfate, filtered and solvent removed under reduced pressure to provide the product as an off white solid (0.035 g, 0.08 mmol, 16% yield). 1H NMR (400 MHz, DMSO-^5) delta 12.07 (bs, IH), 9.23 (s, IH), 8.95 (s, IH), 8.59 (m, 2H), 7.93 (m, 2H), 7.78 (m, 2H), 7.63 (bs, IH); MS (ESI) m/z 435.0 [M+l]+; mp 230-2320C.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 113118-82-4, 5-Chloronicotinaldehyde.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2008/51494; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde. A new synthetic method of this compound is introduced below.

Hydroxylamine hydrochloride (2.3 g) and sodium acetate (2.7 g) were initially charged in ethanol (50 ml) under nitrogen (white suspension). 5-Chloronicotinaldehyde (4.3 g) were dissolved in ethanol (120 ml) (30 C., ultrasound bath) and added dropwise thereto within 15 minutes. The reaction mixture was stirred for 2 hours and concentrated at 40 C. Dichloromethane (550 ml) and water (250 ml) were added and the resulting precipitate is filtered off and dried. Yield: 2.1 g of 5-chloronicotinaldehyde oxime

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; BAYER CROPSCIENCE AG; Frenzel, Thomas; Haaf, Klaus Bernhard; Lindell, Stephen David; Willms, Lothar; Dietrich, Hansjoerg; Schmutzler, Dirk; Gatzweiler, Elmar; Rosinger, Christopher Hugh; US2015/223461; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.113118-82-4, name is 5-Chloronicotinaldehyde, molecular formula is C6H4ClNO, molecular weight is 141.5551, as common compound, the synthetic route is as follows.COA of Formula: C6H4ClNO

General procedure: Oleanolic acid analogues 4e29 were obtained from Scheme 1.Firstly, oleanolic acid (0.66 mmol) and selectfluor (1-chloromethy l-4-fluoro-1, 4-diazoniabicyclo [2.2.2] octane bis (tetrafluoroborate))(1.98 mmol) were dissolved in the mixed solution of anhydrousdioxane (4 mL) and nitromethane (6 mL), and stirred at 80 C for4 h. Then the reaction mixture was concentrated under reducedpressure, extracted with ethyl acetate and deionized water, filteredand dried with anhydrous magnesium sulfate. Next, the crudeproduct was purified on a silica gel column with petroleum ether/ethyl acetate (v/v 5:1) as the eluent to obtain the intermediate OA-F.Secondly, OA-F (0.51 mmol) was added into 75 mL of acetone andstirred at 0 C until it was completely dissolved. Then the Jonesreagent (0.5 mL) was slowly added into the solution and stirred for5 min. After pretreatment similar with OA-F, the crude product waspurified via dichloromethane/petroleum ether (v/v 2:1/3:1) asthe eluent on silica gel column to produce another intermediateOA-F-01. Finally, OA-F-01 (0.44 mmol) and potassium hydroxide(0.88 mmol) were dissolved in the mixed solution of dichloromethane(10 mL) and ethanol (10 mL) followed by adding aldehyde(0.88 mmol) and stirring at room temperature for 12 h. After pretreatmentsimilar with OA-F and OA-F-01, petroleum ether/dichloromethane or ethyl acetate were used as the eluent to purifythe crude product for gaining the analogues 4-29.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Article; Zhong, Ying-Ying; Chen, Hui-Sheng; Wu, Pan-Pan; Zhang, Bing-Jie; Yang, Yang; Zhu, Qiu-Yan; Zhang, Chun-Guo; Zhao, Su-Qing; European Journal of Medicinal Chemistry; vol. 164; (2019); p. 706 – 716;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde. A new synthetic method of this compound is introduced below.

n-Butyllithium (2.063ml, 5.16 mmol) was added to -40 C solution of 1 -bromo-4-(trifluoromethyl)benzene (0.722 ml, 5.16 mmol) in THF (30 ml) and this solution was stirred at -40 C for 1 h. A solution of 5-chloronicotinaldehyde (730 mg, 5.16 mmol) in THF (5 mL) was added and the solution was stirred at -40 C for 1 h and then at 0 C for 1 h. The reaction was then quenched with saturated aqueous NH4C1 solution. The product was extracted with ethyl acetate. The organic extract was dried over Na2504, filtered, and concentrated. No further purification is necessary. ?H NMR (500 MHz, CDC13) oe: 8.54 (s, 1H), 8.48 (s, 1H), 7.78 (s, 1H), 7.66 (d, J= 8 Hz, 2H), 7.53 (d, J= 8 Hz, 2H), 5.97(s, 1H), 3.55 (broad s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; WILSON, Jonathan, E.; MCCRACKEN, Troy; (95 pag.)WO2016/179059; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 113118-82-4, 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. 113118-82-4, name is 5-Chloronicotinaldehyde. A new synthetic method of this compound is introduced below.

n-Butyllithium (2.063ml, 5.16 mmol) was added to -40 C solution of 1 -bromo-4-(trifluoromethyl)benzene (0.722 ml, 5.16 mmol) in THF (30 ml) and this solution was stirred at -40 C for 1 h. A solution of 5-chloronicotinaldehyde (730 mg, 5.16 mmol) in THF (5 mL) was added and the solution was stirred at -40 C for 1 h and then at 0 C for 1 h. The reaction was then quenched with saturated aqueous NH4C1 solution. The product was extracted with ethyl acetate. The organic extract was dried over Na2504, filtered, and concentrated. No further purification is necessary. ?H NMR (500 MHz, CDC13) oe: 8.54 (s, 1H), 8.48 (s, 1H), 7.78 (s, 1H), 7.66 (d, J= 8 Hz, 2H), 7.53 (d, J= 8 Hz, 2H), 5.97(s, 1H), 3.55 (broad s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,113118-82-4, 5-Chloronicotinaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; SHEN, Dong-Ming; WILSON, Jonathan, E.; MCCRACKEN, Troy; (95 pag.)WO2016/179059; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem