Author: tianli

Related Products of 39590-81-3 ,Some common heterocyclic compound, 39590-81-3, molecular formula is C5H10O2, 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.

1. Iodination of 6 to Prepare 7a: [0145] Triphenylphospine (257.2 g) and imidazole (66.7 g) were charged to a reactor. DCM (490 mL) was charged, agitation was initiated and the solution was cooled to 0 C. Iodine (249.2 g) was added as a solid portion-wise over 1 h while maintaining the internal temperature below 10 C. Upon completion of the addition, a solution of 6 (50 g) in DCM (113 mL) was slowly charged to the reactor over 0.5 h while maintaining the internal temperature below 10 C. After stirring for 2.5 h, an aqueous solution of NaCl (25 g) in water (225 mL) was charged to the reactor. Following phase separation, the bottom organic layer was diluted with n-heptane (550 mL). The organic phase was washed with an aqueous solution of sodium sulfite (21 g) in water (190 mL). Following layer separation, the organic phase was concentrated to 600 mL via vacuum distillation. Additional n-heptane (550 mL) was charged, and the mixture was again concentrated to 600 mL via vacuum distillation. The resulting slurry was filtered over a silica gel plug (85 g) that had been slurry packed with n-heptane. The silica gel plug was rinsed with additional n-heptane (1 L), and the filtrate was then concentrated via vacuum distillation to provide the desired product 7a as a colorless liquid (114 g, 70%). 1H NMR (400 MHz, CDCl3) delta 3.33 (s, 2H), 0.95 (s, 2H). 13C NMR (75 MHz, CDCl3): 19.1, 22.7, 26.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,39590-81-3, its application will become more common.

Reference:
Patent; Gilead Sciences, Inc.; Scott, Robert William; Vitale, Justin Philip; Matthews, Kenneth Stanley; Teresk, Martin Gerald; Formella, Alexandra; Evans, Jared Wayne; US2013/324740; (2013); A1;,
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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. 89-95-2, name is 2-Methylbenzyl alcohol, molecular formula is C8H10O, 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. Quality Control of 2-Methylbenzyl alcohol

General procedure: To a mixture of the benzyl alcohol (1 mmol)and formic acid (3 mmol); 0.1 g tribromoisocyanuricacid (0.3 mmol) was added. The reaction mixturewas stirred at room temperature for 5 min. Aftercompletion of the reaction (TLC), dichloromethane(10 mL) was added to the reaction mixture andfiltered. The product was extracted with H2O (3¡Á10mL), and the organic layer was dried over anhydrousNa2SO4salt. Evaporation of the solvent underreduced pressure to give the almost pure product.

With the rapid development of chemical substances, we look forward to future research findings about 89-95-2.

Reference:
Article; Hekmatian, Zahra; Khazaei, Ardeshir; Oriental Journal of Chemistry; vol. 31; 3; (2015); p. 1565 – 1570;,
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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. 145691-59-4, name is (3,5-Dibromophenyl)methanol, the common compound, a new synthetic route is introduced below. Quality Control of (3,5-Dibromophenyl)methanol

To a cooled (dry ice) mixture of 3, 5 -dibromobenzyl alcohol (1 g, 3.8 mmol) and PdCl2(dppf)[0.07 eq] in dry THF (10 mL) was added 1.1 M Et2Zn (15 mL, 16 mmol, 4.4 eq). The resulting mixture was allowed to warm to RT, stirred at 45¡ãC (programmed block temperature, overnight). To bring the reaction to completion (disappearance of both starting material and monoalkylated product) additional 1.1 M Et2Zn (10 mL, 11 mmol, 2.9 eq) was added with continued stirring at 45¡ãC (again overnight). After cooling, the reaction mixture was then added to a stirred mixture of dilute HCl and heptane/EtOAc (2: 1; -200 mL), and the organic layer was dried (Na2S04), filtered, and evaporated. Chromatography (10percent> EtO Ac/heptane) gave 0.33 g (yield of 53percent) of title product. 1H NMR (300 MHz, CDC13) delta 1.22 (t, 6 H), 1.65 (br s, 1 H), 2.61 (q, 4 H), 4.66 (s, 2 H), 6.95-7.05 (m, 3 H).

The synthetic route of 145691-59-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; GLICK, Gary, D.; HURD, Alexander, Ross; VAN HUIS, Chad, Alan; WO2011/35124; (2011); A1;,
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Application of 597-31-9, 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.597-31-9, name is 3-Hydroxy-2,2-dimethylpropanal, molecular formula is C5H10O2, molecular weight is 102.1317, as common compound, the synthetic route is as follows.

2,2-Dimethyl-3-hydroxypropionaldehyde (Hydroxypivalaldehyde, Mitsubishi Gas Chemical Co., Ltd., Purity 99.8%), 59.6 g of 2-ethyl-2-hydroxymethylpropane-1,3-diol (trimethylolpropane, Tokyo Chemical Industry Co., Ltd. reagent), 706 g of benzene, Granular Nafion (trade name “NR-50” Sigma Aldrich Reagent) 5.0 g in a 2-liter round bottom flask, Water generated under atmospheric pressure was withdrawn out of the system using a Dean-Stark trap while azeotropically boiling with benzene, The reaction was allowed to proceed until distillation of water stopped. This was filtered and recrystallized by concentration and cooling, To give crystals of 2- (5-ethyl-5-hydroxymethyl- [1,3] dioxan-2-yl) -2-methylpropan-1-ol.

The chemical industry reduces the impact on the environment during synthesis 597-31-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Mitsubishi Gas Chemical Co., Ltd.; Ikeno, Kento; Yokobori, Umi; Sato, Hideyuki; Hasemi, Takashi; (26 pag.)JP2016/84286; (2016); A;,
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Synthetic Route of 261762-59-8 , The common heterocyclic compound, 261762-59-8, name is 2-Chloro-5-fluorobenzyl alcohol, molecular formula is C7H6ClFO, 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.

Conversion 4, step 4C; Preparation of 5-(2-chloro-5-fluoro-benzyloxy)-3-{4-(4-methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2- trifluoro-acetylj-aminol-benzoylaminoj-indazole-i-carboxylic acid tert-butyl ester; Triphenylphosphine (146 mg, 0.557 mmol) in DCM (2 mL), cooled at 4C, in a nitrogen atmosphere was treated with neat diisopropyl azodicarboxylate (0.106 mL, 0.5208 mmol) while stirring. After 20 minutes the colourless solution was treated with 5-hydroxy-3-{4-(4-methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]- benzoylamino}-indazole-1-carboxylic acid tert-butyl ester (82 mg, 0.5108 mmol) in DCM (2 mL). After 2 hours the crude was purified by flash chromatography over silica gel (DCM:EtOH:35% NH4OH 95:5:0.5) and 108 mg of title compound were obtained as a white solid in 59 % yield. ESI(+) MS: m/z 790 (MH+).

The synthetic route of 261762-59-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; MENICHINCHERI, Maria; BERTRAND, Jay, Aaron; MARCHIONNI, Chiara; NESI, Marcella; ORSINI, Paolo; PANZERI, Achille; WO2010/69966; (2010); A1;,
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Application of 108-82-7, 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. 108-82-7, name is 2,6-Dimethylheptan-4-ol, molecular formula is C9H20O, 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.

General Procedure for Carbamate FormationThe desired alcohol (1.0 equiv.) was dissolved in DCM (0.3 M) in a flame-dried round- bottom flask under a nitrogen atmosphere at 00C. Pyridine (1.0 equiv.) was added followed by 2,2,2- trifluoroethylisocyanate solution (1.0 equiv., stored at -200C) added dropwise. The resulting solution was warmed to ambient temperature and stirred for two hours or until TLC showed complete consumption of the alcohol. The crude reaction was concentrated in vacuo. Flash chromatography (silica gel, DCM) provided the corresponding carbamate .; Compound 1 : Yield: 0.533 g, 97%Physical State: white solid mp: 42-43 0C Rf: 0.65 (silica gel, DCM)IR (film) Vmax: 3462, 3016, 2970, 2359, 1739, 1522, 1366, 1229, 1156 cm”11H mm (500 MHz, CDCl3) : delta 5.11-5.09 (m, 1 H) , 4.96- 4.93 (m, 1 H) , 3.79-3.74 (m, 2 H) , 1.62-1.58 (m, 2 H) , 1.48-1.46 (m, 2 H) , 1.29-1.25 (m, 2 H) , 0.90-0.88 (m, 12 H)13C NMR (125 MHz, CDCl3) : delta 156.4, 127.7-121.0 (q, J = 277 Hz) , 73.3, 44.3, 43.1-42.3 (q, J = 34 Hz) , 24.8, 23.2, 22.4HRMS (ESI) : calcd. for Ci2H22F3NO2Na [M + Na+] 292.1495, found 292.1498

According to the analysis of related databases, 108-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2009/137691; (2009); A2;,
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Adding a certain compound to certain chemical reactions, such as: 101597-25-5, 1,1-Bis(4-methoxyphenyl)prop-2-yn-1-ol, 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, 101597-25-5, blongs to alcohols-buliding-blocks compound. HPLC of Formula: C17H16O3

Step 7; The product of Step 6 (4.8 g), was dissolved in dichloromethane (150 mL) in a 3-necked 100 mL round bottom flask, followed by addition of p-toluenesulfonic acid monohydrate (0.4 g). 1 ,1-Bis(4-methoxyphenyl)-2-propyn-1-ol (3.8 g) was added to the reaction mixture slowly. The mixture was stirred at room temperature. After one hour, more 1 ,1-bis(4-methoxyphenyl)-2- propyn-1-ol, (0.4 g) was added to the reaction mixture. After stirring for two hours, the reaction was worked up with the addition of saturated aqueous NaHC03 (100 mL). The resulting organic layer was collected and dried over anhydrous MgS04. The organic layer was concentrated under vacuum to provide product (8.7 g). The product was purified by column chromatography using silica gel and as eluent, a mixture of hexanes/EtOAc,( v/v, 4/1 ) to yield 2 g product. The product was foamed under vacuum and scratched with spatula to provide a solid material. The solid was slurried over methanol (30 mL), filtered and washed with methanol (2 x 20 mL) to provide a grayish product (1.4 g). NMR analysis of the product indicated a structure that was consistent with 3,3-bis-(4-methoxyphenyl)-7-chloro-13,13-dimethyl-3H, 13H- indeno[2′,3′:3,4]naphtho[1 ,2-b]pyran represented by the following graphic formula:

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,101597-25-5, its application will become more common.

Reference:
Patent; TRANSITIONS OPTICAL, INC.; WO2012/82999; (2012); A1;,
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Application of 111-45-5 ,Some common heterocyclic compound, 111-45-5, molecular formula is C5H10O2, 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: The designated donor (i.e. 19, 0.025 mmol) and the acceptor (2-2.5eq.) were dissolved in dry DCM (2-3 mL) under N2 in presence of freshly activated 4 A molecular sieves. The mixture was stirred for 1-1.5 h at rt and then cooled to -20 C. TMSOTf (0.5-1.0 eq.~10muL neat, or as a solution of 50 muL dissolved in 0.5 mL DCM) was added to the reaction and the mixture was allowed to warm to rt over a period of 2h. Upon completion, as monitored by TLC, the reaction was neutralized by adding TEA (50 muL) and filtered. The solvent was removed under reduced pressure and the crude material was purified by column chromatography using 4:1 Hex:EtOAc as eluent to obtain the product glycosides

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. 111-45-5, 2-(Allyloxy)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Saha, Jaideep; Peczuh, Mark W.; Tetrahedron Letters; vol. 53; 42; (2012); p. 5667 – 5670;,
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Application of 3637-61-4, 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. 3637-61-4, name is Cyclopentanemethanol. A new synthetic method of this compound is introduced below.

To a suspension of NaH (61 mg, 1.5 mmol) in THF (3 mL) at 0C was added CpMeOH (0.16 mL, 1.5 mmol). After 30 min at 0C, 6-(6-bromopyridin-2-yl)-3-((2- chlorophenyl)thio)-6-(thiophen-3-yl)piperidine-2,4-dione (150 mg, 0.30 mmol) was added and the reaction mixture was stirred for 18 hr at reflux. The reaction was stopped by the addition of water (10 mL) and HC1 1 M (3 mL). The aqueous phase was extracted with ethyl acetate (3 x 10 mL) and the combined organic phases were dried over Na2S04, filtered and concentrated under reduced pressure. The crude material was purified by flash column chromatography (silica gel, eluent: heptane/ethyl acetate: 8/2 to 7/3 to 1/1) to give 3-((2-chlorophenyl)thio)-6-(6- (cyclopentylmethoxy)pyridin-2-yl)-6-(thiophen-3-yl)piperidine-2,4-dione in 62 % yield. 1H NMR (400 MHz, MeOH-d4): delta = 7.70 (t, J = 7.8 Hz, 1H), 7.43 (dd, J = 5.0, 3.0 Hz, 1 H), 7.28 (br s, 1 H), 7.22 (d, J= 7.9 HZ, 1 H), 7.15-7.12 (m, 2H), 6.94 (t, J= 7.8 Hz, 1 H), 6.77-6.73 (m, 2H), 5.98 (d, J= 8.0 Hz, 1H), 4.22 (m, 2H9, 3.91 (d, J= 16.4 Hz, 1 H), 3.45 (d, J= 16.4 Hz, 1H), 3.45 (s, 1H), 2.35-2.28 (m, 1H), 1.82-1.73 (m, 2H), 1.64-1.51 (m, 4H), 1.38-1.30 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,3637-61-4, Cyclopentanemethanol, and friends who are interested can also refer to it.

Reference:
Patent; ARCTIC PHARMA AS; GOLDING, Louise; KLAVENESS, Jo; SIENG, Bora; LUNDVALL, Steffi; B?EN, Claudia Alejandra; HNIDA, Kathrin; (128 pag.)WO2018/211277; (2018); A1;,
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Reference of 27489-62-9, 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. 27489-62-9, name is trans-4-Aminocyclohexanol, molecular formula is C6H13NO, 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.

To a mixture of 2-(4,6-dichloropyrimidin-5-yl)acetaldehyde (5.0 g, 26.3 mmol) and (1 R.4R)- 4-aminocyclohexanol (3.0 g, 26.3 mmol) in EtOH (66 mL) was added DIEA (5.5 mL, 31.6 mmol). The reaction was heated at 80C overnight. The reaction mixture was cooled to room temperature, concentrated in vacuo, and purified by silica gel flash column chromatography (MeOH/ DCM: 0-10 %) to afford the title compound. MS m/z 252.0 (M + H+) (Method M).

According to the analysis of related databases, 27489-62-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NOVARTIS AG; IRM LLC; CHEN, Bei; FAIRHURST, Robin, Alec; FLOERSHEIMER, Andreas; FURET, Pascal; GUAGNANO, Vito; JIANG, Songchun; LU, Wenshuo; MARSILJE, Thomas, H.; MCCARTHY, Clive; MICHELLYS, Pierre-Yves; STAUFFER, Frederic; STUTZ, Stefan; VAUPEL, Andrea; WO2011/29915; (2011); A1;,
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