Month: February 2021

Synthetic Route of 2854-16-2, 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. 2854-16-2, name is 1-Amino-2-methylpropan-2-ol. A new synthetic method of this compound is introduced below.

To a solution of V-2 (10 mg, 0.020 mmol) in DMF (1 mL) were added l-amino-2- methylpropan-2-ol (9.13 mg, 0.102 mmol), DIEA (0.036 mL, 0.205 mmol) and HATU (14.01 mg, 0.037 mmol) at rt. The reaction was stirred under argon at rt for 1.5 h. Purification by reverse phase chromatography afforded Example V-3 as white solid (9.0 mg, 98percent). LC-MS (ESI) m/z: 446.1 [M+H]+; XH NMR (500MHz, DMSO-d6) 5 9.18 (br. s., 1H), 8.61 (d, J=4.7 Hz, 1H), 8.54 (s, 1H), 8.21 (br. s., 1H), 8.09 (d, J=8.0 Hz, 1H), 7.88 (d, J=5.0 Hz, 1H), 7.83 (s, 1H), 7.75 (d, J=7.4 Hz, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.53 (s, 1H), 7.50 – 7.45 (m, 1H), 7.45 – 7.38 (m, 1H), 5.52 (q, J=6.2 Hz, 1H), 4.62 – 4.47 (m, 3H), 3.25 (d, J=5.8 Hz, 2H), 1.58 (d, J=6.3 Hz, 3H), 1.10 (s, 6H); Analytical HPLC RT E: 0.99 min, F: 1.27 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,2854-16-2, 1-Amino-2-methylpropan-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; QUAN, Mimi L.; HU, Zilun; WANG, Cailan; PATIL, Sharanabasappa; WO2015/2915; (2015); A1;,
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Related Products of 140373-17-7 , The common heterocyclic compound, 140373-17-7, name is 2-Amino-2-(4-fluorophenyl)ethanol, molecular formula is C8H10FNO, 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.

Example 47: Preparation of 2-[6-(3-chloro-phenyl)-pyrazin-2-ylamino]-2-(4-fluoro- phenyl)-ethanol Under an Ar atmosphere, a mixture of 2-chloro-6-(3-chloro-phenyl)-pyrazine (112.5 mg, 0.5 mmol) and 2-amino-2-(4-fluoro-phenyl)-ethanol (230 mg, 1.5 mmol) was exposed to microwave irradiation at 180 C for 1 hour. After the reaction was completed as monitored by LC-MS, the residue was partitioned between EtOAc and brine. The aqueous layer was separated and then extracted with EtOAc. The combined organic layers were concentrated, and then the residue was purified by Prep-HPLC to give 2-[6-(3-chloro-phenyl)-pyrazin-2-ylamino]-2-(4- fluoro-phenyl)-ethanol (10 mg).

The synthetic route of 140373-17-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; WANG, Jianhua; WANG, Min; YANG, Song; ZHOU, Chengang; WO2014/106606; (2014); A1;,
Alcohol – Wikipedia,
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Related Products of 112-27-6 ,Some common heterocyclic compound, 112-27-6, molecular formula is C6H14O4, 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.

To a stirred solution of 2,2?-(ethane-1,2-diylbis(oxy))bis(ethan-1-ol) (30 g, 200 mmol) in THF (125 mL) was added 60% NaH in paraffin (4 g, 100 mmol) at 10 C. The resulting reaction mixture stirred at the same temperature for 0.5 h. To this reaction mixture was then added benzyl bromide (17 g, 100 mmol) in THF (125) dropwise at 10 C. over 1.5 h. The resulting reaction mixture then stirred at rt for 16 h. The reaction mixture was then transferred into ice water and the resulting mixture was extracted using DCM (3¡Á100 mL). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the crude product was purified using silica gel column chromatography (4% MeOH-DCM) to give 2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethan-1-ol as a yellow oil (20 g, 42%). LC-MS (ESI+) m/z 241.35 (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,112-27-6, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); 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. 14320-38-8, name is Cyclopent-3-enol, molecular formula is C5H8O, 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. name: Cyclopent-3-enol

To a solution of 3-cyclopentene-1-ol (7.0 g, 83.0 mmol) and Et3N (14.5 g, 143.0 mmol) in CH2Cl2 (200 mL) was added 4-nitrobenzoyl chloride (18.5 g, 100.0 mmol) as solid in several portions over a period of 30 min. The resulting suspension was stirred at room temperature over night. The precipitate was filtered off and the filtrate was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage SP1; column 40M; TLC method: n-hexane/ethyl acetate 9/1; Rf=0.50), affording the title product (15.6 g, yield 81%): 1H NMR (500 MHz, CDCl3) delta 8.28 (d, J=8.9 Hz, 2H), 8.20 (d, J=8.9 Hz, 2H), 5.81 (m, 2H), 5.69 (m, 1H), 2.95 (m, 2H), 2.61 (m, 2H).

With the rapid development of chemical substances, we look forward to future research findings about 14320-38-8.

Reference:
Patent; ALI, Amjad; Sebhat, Iyassu K.; Franklin, Cristopher L.; Rupprecht, Kathleen M.; Baker, Robert K.; Nargund, Ravi P.; Yan, Lin; Huo, Pei; Shen, Dong-Ming; Almirante, Nicoletta; Biondi, Stefano; Ferrario, Massimiliano; Nicotra, Alessia; US2010/29678; (2010); A1;,
Alcohol – Wikipedia,
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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. 111-45-5, name is 2-(Allyloxy)ethanol, molecular formula is C5H10O2, 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. Recommanded Product: 2-(Allyloxy)ethanol

30.6 g (0.3 mol) of allyloxyethanol was dissolved in 100 ml of methylene chloride,Further, a solution prepared by adding 33.4 g (0.33 mol) of triethylamine and 1.8 g (0.015 mol) of N, N-dimethylaminopyridine was prepared.next,The obtained solution was cooled with ice,To this solution,A solution of 31.4 g (0.3 mol) of methacrylic acid chloride in 50 ml of methylene chloride was added dropwise.After completion of the dropwise addition,After stirring at room temperature for 3 hours,100 ml of distilled water was added,It was extracted three times with methylene chloride.Next, the obtained methylene chloride layer was removed using a rotary evaporator to remove the solvent, and the residue obtained was dissolved in 100 ml of toluene to obtain a toluene solution.Then, this toluene solution was washed three times with 0.5 N hydrochloric acid solution,Washed three times with saturated saline solution,And dried with magnesium sulfate solution.After drying, the magnesium sulfate solution was filtered off,The filtrate was concentrated on a rotary evaporator to obtain a concentrate.further,The concentrate was vacuum dried,Methacrylic acid-allyloxyethyl 46.0 g (yield 90%).

With the rapid development of chemical substances, we look forward to future research findings about 111-45-5.

Reference:
Patent; TOKUYAMA DENTAL CORPORATION; AKIZUMI, HIRONOBU; SAKATA, EIBU; (52 pag.)JP2017/141212; (2017); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 623-04-1, name is (4-Aminophenyl)methanol, the common compound, a new synthetic route is introduced below. Safety of (4-Aminophenyl)methanol

A i00-mL, three-necked, round-bottomed flask, was equipped with a magnetic stimng bar, a retlux condenser, and a pressure-equalizing dropping funnel that was connected to a nitrogen flow line and charged with a solution of 97% di-tert-butyl dicarbonate (4.04 g, 18.5 nimol) in tetralydrofuran (30 mid). Amino benzyi alcohol (2.5 g, 20.3 mmol) was placed in the flask and suspended in tetrahydrofuran (65 mL) and 99% triethylamine (3.1 mL, 22 mmoi). The resultmg white suspension was cooled with an ice-water bath and the solution of di-tert-butyl dicarbonate was added dropwise over a period of 30 minutes. After 10 mm of additional stirring, the ice-water bath was removed and the suspension was stirred overnight at room temperature, then warmed at 50C for a further 3 hours. T he solvent was removed tinder reduced pressure and the residue partitioned between EtOAc (50 mL) and saturated aqueous bicarbonate solution (50 mL). The aqueous phase was extracted with three 50-ni. portions of EtOAc. The combined organic phases were dried with anhydrous MgSO4 and concentrated under reduced pressure to give 3.72 g (83% yield) of the product as a brown oil that was used without further purification. ?H NMR (as rotamers) (400 MHz, CDCh) 6 9.26 (s, I H), 8.64 (s, iH), 7.39 (.4H), 7.20 (4H), 5,75 (s, 1H), 5.05 (2H), 4.49 -4.35 (m, 4H), i.47 (s, 9H), 1.40 (s, 1H).

The synthetic route of 623-04-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF WASHINGTON THROUGH ITS CENTER FOR COMMERCIALIZATION; UNIVERSITY OF MONTANA; BUTTRICK, Brian; GUILLOTEAU, Nicolas; DIAZ, Philippe; ISOHERRANEN, Nina; WO2015/26990; (2015); A2;,
Alcohol – Wikipedia,
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Reference of 83647-43-2, 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.83647-43-2, name is (3-Bromo-2-methylphenyl)methanol, molecular formula is C8H9BrO, molecular weight is 201.0605, as common compound, the synthetic route is as follows.

A mixture of compound 2 (4.6 g, 22.8 mmol), phenylboronic acid 3 (5.65 g, 46.3 mmol) and [ 1 , 1 ‘ -bis (diphenylphosphino) – ferrocene ] dichloropalladium ( I I ) dichloromethane complex (0.188 g, 0.103 mmol) in toluene (34.5 mL) and ethanol (11.3 mL) was placed under argon. To this solution sodium bicarbonate, 2M (34.5 mL, 69.0 mmol) was added and the mixture was heated at 80 C for 30 min. Ethyl acetate (44 mL) and (11 mL) water were added to the reaction mixture. The organic extract was concentrated by rotatory evaporation. The crude product was chromatographed on silica gel eluting with 0-40% ethyl acetate in hexane to afford 4.58 g of an off-white solid, mp: 58.0- 59.5 C; 1H NMR (600 MHz, CDC13) delta [ppm] : 7.43-7.40 (m, 3H) , 7.35 (m, 1H) , 7.31-7.29 (m, 2H) , 1H) , 7.26 (t, J=7.6 Hz, 1H) , 7.20 (dd, Jl=7.6 Hz, J2=1.3 Hz, 1H) , 4.78 (s, 2H) , 2.25 (s, 3H) ; 13C NMR (151MHz, DMSO-d6) delta [ppm]: 143.0, 142.2, 140.0, 133.8, 129.7, 129.5, 128.2, 127.0, 126.9, 125.7, 64.2, 16.0; IR V (ATR cm-1) : 3365, 3054, 1601, 1469, 1047, 757.

The chemical industry reduces the impact on the environment during synthesis 83647-43-2, I believe this compound will play a more active role in future production and life.

Reference:
Patent; RIJKSUNIVERSITEIT GRONINGEN; DOeMLING, Alexander; (85 pag.)WO2017/118762; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Synthetic Route of 20712-12-3 , The common heterocyclic compound, 20712-12-3, name is (2-Amino-5-bromophenyl)methanol, molecular formula is C7H8BrNO, 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.

b) Lambda/-[4-Bromo-2-(hydroxymethyI)phenyl]-2-chloroacetamideTo a suspension of Intermediate 28a (2.48 g) in dry Et2O (70 mL) at 00C was added dropwise a solution of chloroacetyl chloride (1.39 g) in dry toluene (25 mL). To the white suspension was added a solution of triethylamine (5.1 mL ) in dry toluene (25 mL). After 1 h the reaction mixture was treated with water and chloroform. The organic phase was dried, filtered, and concentrated in vacuo to give a brown oil (4.45 g) containing the title compound; ESMS m/z 278.0/280.0 [M+H]+ and the bis acetylated compound {5-bromo-2- [(chloroacetyl)amino]phenyl}methyl chloroacetate; ESMS m/z 352.0/354.0/356.0 [M+H]+

The synthetic route of 20712-12-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/50940; (2006); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Reference of 29683-23-6, Adding some certain compound to certain chemical reactions, such as: 29683-23-6, name is Tetrahydro-2H-thiopyran-4-ol,molecular formula is C5H10OS, 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 29683-23-6.

Methi 7-cyciopropyl-6-hydroxypyrazoio[1 ,5-a]pyridine-3-carboxyiate (0. 100 g. 0.431 rnrnoi), tetrahydro-2H-thiopyram4oi (0.102 g, 0.861 mmoi), and 1,1 (azodicarbonvl)dipiperi dine (0.326 g. 1.29 rnmol) were placed in a pressure vial. Then, anhydrous Ph]?ie (4 rnL) and tri-N-butyiphosphine (0.323 rnL, 1.29 rnmoi) were added,and the reaction mixture was stirred at 140 C under microwave irradiation for 15 mm. The reaction mixture was quenched with MeOl-I (5 mL), diluted with MeOH/DCM (20 mE), and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (0-50% EIOAc/DCM gradient) to give methyl 7-cyciopropyl-6- ((tetrahydro-2H-thiopyran-4-yl)oxy)pyrazoio[ I ,5-ajpyridine-3-carboxylate (0.134 g, 94% yield) as a colorless syrup. MS (ESI) ,n??: 333.1 (M-HH). ?H-NMR: (500 MHz,CDCI3) oe ppm 8.38 (s, 11-1), 7.99 (d, J:::94 Hz, 1K), 7.22 (d. J=9.6 Hz, iii), 4.31 4.22(m, 11:1), 3.90 (s, 31:1), 2.97 – 2.88 (in. 2H). 265 2.55 (m, 21:1), 2.44 – 2.36 (in. 1K). 230220 (m, 2H), 2.08 – 1.98 (m, 2H), 1.46 – 139 (m, 2H), 1.21 – 1.15 (m, 2H),

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. 29683-23-6, Tetrahydro-2H-thiopyran-4-ol, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMITH II, Leon M.; LADZIATA, Vladimir; DELUCCA, Indawati; PINTO, Donald, J., P.; ORWAT, Michael J.; DILGER, Andrew K.; PABBISETTY, Kumar Balashanmuga; YANG, Wu; SHAW, Scott A.; GLUNZ, Peter W.; PANDA, Manoranjan; (612 pag.)WO2017/123860; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 702-23-8, 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. 702-23-8, name is 2-(4-Methoxyphenyl)ethanol. A new synthetic method of this compound is introduced below.

PREPARATION F 4-(3-[p-Methoxyphenyl]propyl)pyridine To a stirred solution of 3.04 g. of 2-(p-methoxyphenyl)ethanol in 10 ml. of benzene, is added dropwise, a solution of 0.72 ml. of phosphorus tribromide in 10 ml. of benzene, at ambient temperature. The mixture is then heated at 60C. for 1 hour. After being cooled to ambient temperature again, the reaction mixture is poured onto 50 g. of crushed ice. A small amount of ether is added, and then the organic phase is separated off, washed sequentially with 0.5N sodium hydroxide and water, and evaporated to dryness. This affords 2.8 g. of 2-(p-methoxyphenyl)ethyl bromide as an oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,702-23-8, 2-(4-Methoxyphenyl)ethanol, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US3983107; (1976); A;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts