Category: 53199-31-8

A common heterocyclic compound, 53199-31-8,Bis(tri-tert-butylphosphine)palladium, 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. 53199-31-8

Example 29 Preparation of 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44) This example describes the synthesis of common ligand mimics of the invention containing a linker group following the reaction scheme shown in . Compound numbers correspond to the numbers in the figure. The compounds 4-allyl-5-(4-fluoro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (compound 42, 500 mg, 2.28 mmol) and 5-(4-bromo-phenyl)-furfural were mixed in dioxane (10 ml), followed by the addition of diisopropylethylamine (0.795 ml, 4.56 mmol). Bis(tri-tert-butylphosphine) palladium (56 mg, 0.109 mmol) was added to the reaction mixture, which then was stirred at a temperature of 90 C. for a period of 1 hour. Volatiles were removed in vacuo, and the residue was diluted in 0.2 N HCl solution, followed by extraction with ethyl acetate. Combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (gradient 7:3 to 9:1 ethyl acetate/hexanes+0.5% MeOH) to give 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44, 375 mg, 42%). 1H NMR (300 MHz, CDCl3) delta 4.55 (d, J=4.7, 2H), 6.31 (td, J=3.2, 16.0, 1H), 6.44 (d, J=16.0, 1H), 6.84 (d, J=3.7, 1H), 7.18 (dd, J=8.5, JHF=8.5, 2H), 7.32 (d, J=3.7, 1H), 7.40 (d, J=8.3, 2H), 7.61 (dd, J=8.5, JHF=5.2, 2H), 7.76 (d, J=8.3, 2H), 9.64 (s, 1H), 10.56 (s, 1H); 13C NMR (300 MHz, CDCl3) delta 43.8, 107.9, 116.3 (d, JCF=22), 123.2, 124.4, 125.6, 127.1, 128.7, 130.3 (d, JCF=9), 132.3, 137.1, 147.0, 152.2, 155.7, 158.9, 164.1 (d, JCF=250), 206.6; MS m/s 389.96 (M+1).

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53199-31-8,Bis(tri-tert-butylphosphine)palladium,its application will become more common.

Reference£º
Patent; Yu, Lin; Dong, Qing; Pierre, Fabrice; Chang, Edcon; Lang, Hengyuan; Qin, Yong; Fang, Yunfeng; Hansen, Mark; Pellecchia, Maurizio; US2004/9526; (2004); A1;,
Chapter 1 An introduction to palladium catalysis
Palladium/carbon catalyst regeneration and mechanical application method

A common heterocyclic compound, 53199-31-8,Bis(tri-tert-butylphosphine)palladium, 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. 53199-31-8

Example 29 Preparation of 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44) This example describes the synthesis of common ligand mimics of the invention containing a linker group following the reaction scheme shown in . Compound numbers correspond to the numbers in the figure. The compounds 4-allyl-5-(4-fluoro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (compound 42, 500 mg, 2.28 mmol) and 5-(4-bromo-phenyl)-furfural were mixed in dioxane (10 ml), followed by the addition of diisopropylethylamine (0.795 ml, 4.56 mmol). Bis(tri-tert-butylphosphine) palladium (56 mg, 0.109 mmol) was added to the reaction mixture, which then was stirred at a temperature of 90 C. for a period of 1 hour. Volatiles were removed in vacuo, and the residue was diluted in 0.2 N HCl solution, followed by extraction with ethyl acetate. Combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (gradient 7:3 to 9:1 ethyl acetate/hexanes+0.5% MeOH) to give 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44, 375 mg, 42%). 1H NMR (300 MHz, CDCl3) delta 4.55 (d, J=4.7, 2H), 6.31 (td, J=3.2, 16.0, 1H), 6.44 (d, J=16.0, 1H), 6.84 (d, J=3.7, 1H), 7.18 (dd, J=8.5, JHF=8.5, 2H), 7.32 (d, J=3.7, 1H), 7.40 (d, J=8.3, 2H), 7.61 (dd, J=8.5, JHF=5.2, 2H), 7.76 (d, J=8.3, 2H), 9.64 (s, 1H), 10.56 (s, 1H); 13C NMR (300 MHz, CDCl3) delta 43.8, 107.9, 116.3 (d, JCF=22), 123.2, 124.4, 125.6, 127.1, 128.7, 130.3 (d, JCF=9), 132.3, 137.1, 147.0, 152.2, 155.7, 158.9, 164.1 (d, JCF=250), 206.6; MS m/s 389.96 (M+1)., 53199-31-8

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,53199-31-8,Bis(tri-tert-butylphosphine)palladium,its application will become more common.

Reference£º
Patent; Yu, Lin; Dong, Qing; Pierre, Fabrice; Chang, Edcon; Lang, Hengyuan; Qin, Yong; Fang, Yunfeng; Hansen, Mark; Pellecchia, Maurizio; US2004/9526; (2004); A1;,
Chapter 1 An introduction to palladium catalysis
Palladium/carbon catalyst regeneration and mechanical application method

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO249,mainly used in chemical industry, its synthesis route is as follows.,53199-31-8

Example 29 Preparation of 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44) This example describes the synthesis of common ligand mimics of the invention containing a linker group following the reaction scheme shown in . Compound numbers correspond to the numbers in the figure. The compounds 4-allyl-5-(4-fluoro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (compound 42, 500 mg, 2.28 mmol) and 5-(4-bromo-phenyl)-furfural were mixed in dioxane (10 ml), followed by the addition of diisopropylethylamine (0.795 ml, 4.56 mmol). Bis(tri-tert-butylphosphine) palladium (56 mg, 0.109 mmol) was added to the reaction mixture, which then was stirred at a temperature of 90 C. for a period of 1 hour. Volatiles were removed in vacuo, and the residue was diluted in 0.2 N HCl solution, followed by extraction with ethyl acetate. Combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (gradient 7:3 to 9:1 ethyl acetate/hexanes+0.5% MeOH) to give 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44, 375 mg, 42%). 1H NMR (300 MHz, CDCl3) delta 4.55 (d, J=4.7, 2H), 6.31 (td, J=3.2, 16.0, 1H), 6.44 (d, J=16.0, 1H), 6.84 (d, J=3.7, 1H), 7.18 (dd, J=8.5, JHF=8.5, 2H), 7.32 (d, J=3.7, 1H), 7.40 (d, J=8.3, 2H), 7.61 (dd, J=8.5, JHF=5.2, 2H), 7.76 (d, J=8.3, 2H), 9.64 (s, 1H), 10.56 (s, 1H); 13C NMR (300 MHz, CDCl3) delta 43.8, 107.9, 116.3 (d, JCF=22), 123.2, 124.4, 125.6, 127.1, 128.7, 130.3 (d, JCF=9), 132.3, 137.1, 147.0, 152.2, 155.7, 158.9, 164.1 (d, JCF=250), 206.6; MS m/s 389.96 (M+1).

With the complex challenges of chemical substances, we look forward to future research findings about Bis(tri-tert-butylphosphine)palladium,belong catalyst-palladium compound

Reference£º
Patent; Yu, Lin; Dong, Qing; Pierre, Fabrice; Chang, Edcon; Lang, Hengyuan; Qin, Yong; Fang, Yunfeng; Hansen, Mark; Pellecchia, Maurizio; US2004/9526; (2004); A1;,
Chapter 1 An introduction to palladium catalysis
Palladium/carbon catalyst regeneration and mechanical application method

Bis(tri-tert-butylphosphine)palladium, cas is 53199-31-8, it is a common heterocyclic compound, the catalyst-palladium compound, its synthesis route is as follows.

B. Synthesis of 3-(1-pyrrolidinyl)phenol 7g (30 mmol) of 1-Bromo-3-methoxymethoxy-benzene from step A and 2,5 g (35 mmol) of pyrrolidine were dissolved under argon in 60 mL of toluene. Then, 0.15 g (0.3 mmol) of bis(tri-t-butylphosphine)palladium(0), 2,5g KOH und 0,6g (0,15 mmol) cetyltrimethylammoniumbromid were added, and the reaction mixture was heated at 80 C. At the end of the reaction, the reaction mixture was poured into 200 mL of ethyl acetate, and the organic phase was extracted with 1 N sodium hydroxide solution and then dried with magnesium sulfate. The solvent was distilled off in a rotary evaporator, and the residue was purified on silica gel using heptane/ethyl acetate (8/0,8). The product thus obtained was dissolved in 15 mL of ethanol and mixed with 10 mL of a 2.9 molar solution of ethanolic hydrochloric acid.

As the rapid development of chemical substances, we look forward to future research findings about 53199-31-8

Reference£º
Patent; Wella Aktiengesellschaft; EP1752192; (2007); A1;,
Chapter 1 An introduction to palladium catalysis
Palladium/carbon catalyst regeneration and mechanical application method

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.53199-31-8,Bis(tri-tert-butylphosphine)palladium,as a common compound, the synthetic route is as follows.

B. Synthesis of 3-(1-pyrrolidinyl)phenol 7g (30 mmol) of 1-Bromo-3-methoxymethoxy-benzene from step A and 2,5 g (35 mmol) of pyrrolidine were dissolved under argon in 60 mL of toluene. Then, 0.15 g (0.3 mmol) of bis(tri-t-butylphosphine)palladium(0), 2,5g KOH und 0,6g (0,15 mmol) cetyltrimethylammoniumbromid were added, and the reaction mixture was heated at 80 C. At the end of the reaction, the reaction mixture was poured into 200 mL of ethyl acetate, and the organic phase was extracted with 1 N sodium hydroxide solution and then dried with magnesium sulfate. The solvent was distilled off in a rotary evaporator, and the residue was purified on silica gel using heptane/ethyl acetate (8/0,8). The product thus obtained was dissolved in 15 mL of ethanol and mixed with 10 mL of a 2.9 molar solution of ethanolic hydrochloric acid.

The synthetic route of 53199-31-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wella Aktiengesellschaft; EP1752192; (2007); A1;,
Chapter 1 An introduction to palladium catalysis
Palladium/carbon catalyst regeneration and mechanical application method

53199-31-8, Bis(tri-tert-butylphosphine)palladium is a catalyst-palladium compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 29 Preparation of 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44) This example describes the synthesis of common ligand mimics of the invention containing a linker group following the reaction scheme shown in . Compound numbers correspond to the numbers in the figure. The compounds 4-allyl-5-(4-fluoro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one (compound 42, 500 mg, 2.28 mmol) and 5-(4-bromo-phenyl)-furfural were mixed in dioxane (10 ml), followed by the addition of diisopropylethylamine (0.795 ml, 4.56 mmol). Bis(tri-tert-butylphosphine) palladium (56 mg, 0.109 mmol) was added to the reaction mixture, which then was stirred at a temperature of 90 C. for a period of 1 hour. Volatiles were removed in vacuo, and the residue was diluted in 0.2 N HCl solution, followed by extraction with ethyl acetate. Combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (gradient 7:3 to 9:1 ethyl acetate/hexanes+0.5% MeOH) to give 5-(4-{3-[3-(4-fluoro-phenyl)-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl]-propenyl}-phenyl)-furan-2-carbaldehyde (compound 44, 375 mg, 42%). 1H NMR (300 MHz, CDCl3) delta 4.55 (d, J=4.7, 2H), 6.31 (td, J=3.2, 16.0, 1H), 6.44 (d, J=16.0, 1H), 6.84 (d, J=3.7, 1H), 7.18 (dd, J=8.5, JHF=8.5, 2H), 7.32 (d, J=3.7, 1H), 7.40 (d, J=8.3, 2H), 7.61 (dd, J=8.5, JHF=5.2, 2H), 7.76 (d, J=8.3, 2H), 9.64 (s, 1H), 10.56 (s, 1H); 13C NMR (300 MHz, CDCl3) delta 43.8, 107.9, 116.3 (d, JCF=22), 123.2, 124.4, 125.6, 127.1, 128.7, 130.3 (d, JCF=9), 132.3, 137.1, 147.0, 152.2, 155.7, 158.9, 164.1 (d, JCF=250), 206.6; MS m/s 389.96 (M+1).

As the paragraph descriping shows that 53199-31-8 is playing an increasingly important role.

Reference£º
Patent; Yu, Lin; Dong, Qing; Pierre, Fabrice; Chang, Edcon; Lang, Hengyuan; Qin, Yong; Fang, Yunfeng; Hansen, Mark; Pellecchia, Maurizio; US2004/9526; (2004); A1;,
Chapter 1 An introduction to palladium catalysis
Palladium/carbon catalyst regeneration and mechanical application method