Month: September 2021

Related Products of 10016-52-1, A common heterocyclic compound, 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, molecular formula is C12H6Br2O, 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.

[0001083] To a solution of Compound 302B (324 mg, 1 mmol) in THF (20 mL) was added n-BuLi (2.5 M, 0.4 mL, 1.06 mmol) under nitrogen at -60 C. It was stirred at -60 C for 0.5 h. And then a solution of diethyl oxalate (0.4 mL, 3 mmol) in THF (5 mL) was added. The mixture was stirred at -60 C for 0.5 h, quenched with saturated ammonium chloride solution (200 mL), extracted with ethyl acetate (20 mL x 3), washed with brine (20 mL), dried over anhydrous sodium sulfate, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 5% v/v) to furnish Compound 302C.

The synthetic route of 10016-52-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel; BRIDGES, Alexander, James; WO2015/42397; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 50548-45-3, These common heterocyclic compound, 50548-45-3, name is 1-Bromodibenzo[b,d]furan, 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.

(4) In a 1L reaction flask, add intermediate c (51.65 g, 100 mmol), 9,9-dimethyl-9H-fluoren-2-amine (20.93 g, 100 mmol), and tris (dibenzylideneacetone). ) Dipalladium (2.75g, 3mmol), tri-tert-butylphosphine (1.21g, 6mmol), sodium tert-butoxide (19.22g, 200mmol), 500ml of toluene, under a nitrogen atmosphere, heated to 110 C for 12h, the liquid The phase monitoring reaction was completed, the temperature was reduced, 1-bromodibenzofuran (24.71 g, 100 mmol) was added, and the temperature was raised to 110 C to continue the reaction for 8 hours. After drying, 51.09 g of intermediate e can be obtained with a yield of 63%

The synthetic route of 50548-45-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuhan Shang Sai Optoelectric Technology Co., Ltd.; Mu Guangyuan; Zhuang Shaoqing; Ren Chunting; (31 pag.)CN110372570; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, A new synthetic method of this compound is introduced below., HPLC of Formula: C18H11BrO

Argon atmosphere, the compound (vii) in a 100mL three-necked flask 1.50g, Compound (xi) 0.87g, bis(dibenzylideneacetone)palladium (0) (Pd(dba)2) 0.11g, tri-t-butylphosphine ((t-Bu)3P) 0.15g, was added to sodium t-butoxide 0.54g, it was heated under reflux for 7 hours in 45mL of toluene solvent. After air-cooling, water was added The organic layer was separated, and the solvent was distilled off. The crude product thus obtained was purified by silica gel column chromatography (dichloro methane and using a mixed solvent of hexane), toluene, and subjected to recrystallization with hexane mixed solvent to give the compound A-41 as a white solid 1.86g (89percent yield).

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; Samsung DisplayCo., Ltd.; Huchiwaki, Junta; Oyama, Hiromi; Miyata, Yasuo; Sakamoto, Naoya; Ueno, Masatsuku; Takada, Echinori; (155 pag.)KR2015/90021; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 103977-79-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 103977-79-3 as follows.

A solution of 3-bromo-2, 4-difluorophenylamine (from Example 2, step b) (5. 2 g, 25 mmol) and 5-fluoro-2- (4, 4,5, 5-tetramethyl- [1, 3,2] dioxaborolan-2-yl) benzonitrile (7.10 g, 28.8 mmol) in tetrahydrofuran (95 ml) and water (5 ml) was treated with potassium fluoride (4.8 g, 82.5 mmol) and this mixture was degassed with nitrogen for 10 min before adding tris (dibenzylideneacetone) dipalladium (0) (460 mg, 0. 5 mmol) and tri-tert-butylphosphine (2.5 ml of a 0.2 M solution in 1,4-dioxane, 0. 5 mmol). The reaction was then heated at 50C for 2 h then cooled to ambient temperature. The mixture was poured into ice-cold 0.5 N sodium hydroxide (750 ml), stirred for 10 min and the solid collected by filtration. This was triturated with water and dried to afford 3′-amino- 4, 2′, 6′-triffuorobiphenyl-2-carbonitrile as a grey powder (6.6 g), which was used without further purification: 1H NMR (360 MHz, Cd13) 8 3.74 (2H, br s), 6.79-6. 89 (2H, m), 7.36-7. 42 (1H, m), 7.45-7. 51 (2H, m).

According to the analysis of related databases, 103977-79-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2003/93272; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1137142-58-5, These common heterocyclic compound, 1137142-58-5, name is 2-Bromoimidazo[2,1-b][1,3,4]thiadiazole, 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 M; 2-(3,4-Dimethoxy-pheny.)-imidazo[2,1-b][1,3,4]thiadiazoleA solution of 2-bromo-imidazo[2,1-b][1,3,4]thiadiazole (0.5 g, 2.5 mmol, 1 eq), 3,4-dimethoxyphenylboronic acid (0.683 g, 3.7 mmol, 1.5 eq), dioxane (12.5 mL) and Na2CO3 (2M aq. solution, 3.8 mL) was degassed for 20 minutes at room temperature. Pd(Ph3P)2CI2 WaS added and the reaction heated at 110 ºC for 2h in an argon atmosphere. The reaction mixture was diluted with EtOAc and washed with water. The combined organic layers were dried (Na2SO4), filtered and concentrated, and the residue was purified by column chromatography (SiO2, cyclohexane / 20-100% ethylacetate). The product was further purified by triturating with Et2O, filtered off and dried affording the desired product (0.080 g). 1H NMR (300 MHz, DMSO) delta/ppm 8.18 (d, J = 1.4, 1 H), 7.47 (m, 2H), 7.33 (d, J = 1.4, 1H), 7.15 (d, J = 8.3, 1H), 3.86 (s, 3H), 3.75 (s, 3H). – The filtrate was concentrated, redissolved in DCM- and purified by flash-chromatography (SiO2, DCM / 1% MeOH) to afford the desired product (0.65 g, containing some Ph3PO) that was used as such in the next step.

The synthetic route of 1137142-58-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; KURZ, Guido; MARTINEZ GONZALEZ, Sonia; WO2010/112874; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 766-81-4 as follows. Safety of 3-Bromophenylacetylene

In a 25 mL roundbottom flask, 1-bromo-3-ethynylbenzene (243 muL, 1.94 mmol, 1.1 equiv) was dissolved in 10 mL THF and cooled to-78 C. A solution of LiHMDS (1 M in THF, 1.9 mL, 1.85 mmol, 1.05 equiv) was added dropwise, then the mixture allow to warm to room temperature and stir for 15 min. The reaction was cooled again to-78 C and a solution of 3-((tert-butyldiphenylsilyl)oxy)propanal (552 mg, 1.77 mmol, 1.0 equiv) in 1.8 mL THF was added by cannula. The reaction was allowed to warm to room temperature and was stirred for 12 hr.10 mL saturated aqueous NH4Cl was added to quench the reaction, followed by 10 mL Et2O, then the aq layer was extracted with Et2O (3 × 10 mL). The combined organic extracts were washed with brine (1 × 10 mL), dried (MgSO4), filtered, and concentrated by rotary evaporation. Purification by silica flash chromatography (10-20% EtOAc/hexanes) yielded the propargyl alcohol as a clear yellow oil (802 mg, 92%). TLC: Rf 0.49 (20% EtOAc/hexanes). 1H-NMR (600 MHz): delta 7.76- 7.64 (m, 4H), 7.56 (t, J = 1.8 Hz, 1H), 7.48- 7.32 (m, 8H), 7.18 (t, J = 7.9 Hz, 1H), 4.92 (td, J = 6.4, 4.3 Hz, 1H), 4.12 (ddd, J = 10.5, 8.2, 3.7 Hz, 1H), 3.89 (ddd, J = 10.3, 5.9, 4.2 Hz, 1H), 3.49 (d, J = 6.4 Hz, 1H), 2.20- 2.07 (m, 1H), 2.03- 1.96 (m, 1H), 1.06 (s, 9H). 13C-NMR (151 MHz): delta 135.5, 134.5, 132.7, 131.5, 130.3, 129.9, 129.7, 127.8, 124.7, 122.0, 91.0, 83.5, 62.2, 61.9, 38.5, 26.8, 19.0.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEMORIAL SLOAN-KETTERING CANCER CENTER; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; THE BROAD INSTITUTE, INC.; UNIVERSITY OF CENTRAL FLORIDA RESEARCH FOUNDATION, INC.; MCKERROW, James; DANDAPANI, Sivaraman; EDWANKAR, Rahul; TAN, Derek, Shieh; FOLEY, Corinne, N.; MOURA-LETTS, Gustavo; VERANO, Alyssa; CHAKRABARTI, Debopam; ROBERTS, Bracken; (258 pag.)WO2017/124087; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H13Br

In a IL three-necked round-bottom flask equipped with a mechanical stirrer and a reflux condenser were introduced DMF (20OmL), l-bromo-3-tert-butylbenzene (54.3g, 0.25mol), crotyl alcohol (65mL, 0.76mol, 3eq), sodium carbonate (66.2g, 0.62mol, 2.5eq), tetrabutyl ammonium bromide (69.5g, 0.25mol, leq), palladium acetate (5.05g, 7.5mmol, 3molpercent) and tri-o-tolyl phosphine (7.6g, 25mmol, O.leq). After stirring for Ih at 90- 1000C, the reaction mixture was cooled toambient temperature. The reaction mixture was filtered over celite. The organic phase thus obtained was diluted with MTBE (50OmL) and washed three times with water (50OmL portions), dried over magnesium sulphate and concentrated. The resulting crude product was distilled with a bulb-to-bulb distillation (3mBar, 1210C) to give a colourless oil (34.7g, gc purity 73percent). The crude product was chromatographed on a silica gel column with 5percent EtOAc in hexane as elution agent giving 3-(3-fert-butylrhohenyl)butanal (12.3g, gc purity 99percent; yield 39percent).Odour: floral, aldehydic, muguet, marine.Analytical data: EPO 1H NMR (400 MHz, CHLOROFORM-d) ppm: 1.33 (d, 3H, J=5.86 Hz); 1.32 (s, 9H); 2.61-2.80 (m, 2H); 3.36 (qt, IH, J=7.16, 6.96 Hz); 7.01-7.07 (m, IH); 7.23-7.27 (m, 3H); 9.72 (t, IH, /=2.08 Hz).13C NMR (101 MHz, CHLOROFORM-^) ppm: 22.15 (q, 1C); 31.35 (q, 3C); 34.53 (d, 1C); 34.66 (s, 1C); 51.83 (t, 1C); 123.49 (d, 1C); 123.55 (d, 1C); 123.91 (d, 1C); 128.30 (d, 1C); 145.06 (s, 1C); 151.48 (s, 1C); 202.04 (d, 1C).MS: m/z (relative intensity) 204 (M+, 12), 189 (31), 171 (4), 161 (30), 147 (100), 145 (81), 130 (17), 119 (24), 117 (23), 115 (21), 105 (25), 91 (36), 77 (14), 65 (8), 57 (52), 41 (31).

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; QUEST INTERNATIONAL SERVICES B.V.; WO2008/53148; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, molecular formula is C6H4BrF2N, 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. Computed Properties of C6H4BrF2N

To a suspension of sodium perborate tetrahydrate (1.04 g, 5 mmol) in acetic acid (20 mL), stirred at 55 C., was added a solution of 4-bromo-2,6-difluoroaniline in acetic acid (10 mL) over 1 hour in a dropwise fashion. After stirring at 55 C. for an additional 3 hours, the solution was allowed to cool to room temperature and filtered. The filtrate was poured into ice, and extracted twice with ethyl acetate. The combined organic extracts were washed successively with 5*100-mL portions of water, brine, dried (MgSO4), and concentrated in vacuo. The resulting residue was purified by column chromatography over silica gel eluted with ethyl acetate:hexanes (1:20) to afford 780 mg of the titel compound as a tan solid. 1H NMR (CDCl3) delta 7.32 (dt, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67567-26-4, its application will become more common.

Reference:
Patent; Charifson, Paul S.; Deininger, David D.; Grillot, Anne-Laure; Liao, Yusheng; Ronkin, Steven M.; Stamos, Dean; Perola, Emanuele; Wang, Tiansheng; LeTiran, Arnaud; Drumm, Joseph; US2004/235886; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 30273-40-6,Some common heterocyclic compound, 30273-40-6, name is 4-Bromo-2,5-dimethylaniline, molecular formula is C8H10BrN, 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.

The reaction mixture of 4-bromo-2,5-dimethylaniline (5g, 25mmol) and (Boc)2O (5.4g, 25mmol) in toluene (60ml) was stirred at 100C for 40hrs under nitrogen. After concentration of the reaction mixture under reduced pressure, 5.82 g (78% yield) of boc-NH-4-bromo-2,5- dimethylaniline,2, was obtained as a white solid by columnchromatography (5 -10% ethyl acetate in hexane).

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-2,5-dimethylaniline, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; PARK, Kyung-Ho; RADU, Nora, Sabina; JOHANSSON, Gary, A.; FENNIMORE, Adam; DELANEY, William, J.; LECLOUX, Daniel, David; WO2011/159872; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, 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 a solution of 3-substituted-2-haloimidazo[4,5-b]pyridine derivative (1 equiv) in NMP, were added terminal acetylene (1.5 equiv) and tetrabutyl ammonium acetate (1.5 equiv). The solution was purged with nitrogen and stirred at room temperature for 0.15 h, at that time PdCl2(PCy3)2 was added. The reaction solution was purged again with nitrogen and then placed in the microwave and heated for 10 to 30 min at 110 C (for iodide and bromide intermediates). When chloro intermediate was used, the reaction contents were heated at 150 C. When TLC and LCMS showed full consumption of starting materials, the reaction mixture was diluted with ethyl acetate, separated the ethyl acetate layer, given water wash, brine wash and was dried over anhydrous sodium sulphate and concentrated to get the crude material. The crude product was directly purified by column chromatography (0-15% hexane/EtOAc) to isolate the 3-alkyl-2-akynyl imidao[4,5-b]pyridine derivatives.

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

Reference:
Article; Sajith, Ayyiliath M.; Muralidharan; Tetrahedron Letters; vol. 53; 39; (2012); p. 5206 – 5210;,
Bromide – Wikipedia,
bromide – Wiktionary