Tag: M.W=200-300

Reference of 99548-55-7, 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 99548-55-7 as follows.

A mixture of potassium acetate (649.2 mg, 6.55 mmol), 1,1?- bis(diphenylphosphino)ferrocene palladium dichloride (159.7 mg, 0.22 mmol),bis(pinacolato)diboron (1108.5 mg, 4.37 mmol) and methyl 4-bromo-2-methylbenzoate (500.0 mg, 2.18 mmol) in 1,4-dioxane (20 mL) was stirred at 110 ¡ãC for 4 h under N2 protection, and evaporated to dryness. The residue was taken up in EtOAc (30 mL), washed with water (20 mL x 2) and brine (20 mL), dried over Mg504 and concentrated. The residue was purified by flash column chromatography (10percent ethyl acetate in petroleum ether, Rf = 0.6) to afford methyl 2-methyl-4-(4,4,5 ,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)benzoate (400 mg, 66.4percent yield) as a yellow oil.

According to the analysis of related databases, 99548-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; RQX PHARMACEUTICALS, INC.; GENENTECH, INC.; CHEN, Yongsheng; SMITH, Peter Andrew; ROBERTS, Tucker Curran; HIGUCHI, Robert I.; PARASELLI, Prasuna; KOEHLER, Michael F. T.; SCHWARZ, Jacob Bradley; CRAWFORD, James John; LY, Cuong Q.; HANAN, Emily J.; HU, Huiyong; YU, Zhiyong; (424 pag.)WO2017/84630; (2017); A1;,
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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. 120974-97-2, name is (E)-Methyl 2-(methoxyimino)-2-(o-tolyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

(1) Methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate (4.74 g) was dissolved in carbon tetrachloride (100 ml), and N-bromosuccinimide (4.89 g) and benzoylperoxide (554 mg) were added thereto. The resultant mixture was heated under reflux for 1 hour and cooled to room temperature. Insoluble materials were removed by filtration. On concentration of the solvent, the residue was purified by silica gel column chromatography with a mixture of hexane and ethyl acetate to give methyl-(E)-2-(2-bromomethylphenyl)-2-methoxyiminoacetate (6.98 g). 1 H-NMR: 3.89 (3H, s), 4.07 (3H, s), 4.34 (2H, s), 7.13-7.17 (1H, m), 7.34-7.47 (3H, m).

The synthetic route of 120974-97-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi Seiyaku Kabushiki Kaisha; US5185342; (1993); A;,
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These common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, 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. category: esters-buliding-blocks

Step 9; methyl ll-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-10-methyl-2-oxo-2,5,6,7,8,10-hexahydro-lH- pyrido [3 ‘,2’ : 7,8] cycloocta [1,2-f] indole-3-carboxylate Crude N-(2-((tert-butyldimethylsilyloxy)methyl)- 1 -methyl-7,8,9, 10-tetrahydro- 1 H- cycloocta[f]indol-5(6H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (-0.60 g, 1.17 mmol) and trimethyl methanetricarboxylate (0.37 g, 1.95 mmol) were mixed together in Ph 0 (2.5 mL). With stirring, the mixture was placed onto a pre-heated heat block at 230 C and heated for 10 min after the initial bubbling of MeOH was observed (occurs at -160 C internal reaction temperature). The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes, followed by EtOAc/hexanes 0-60% gradient) to yield the product as a yellow foam (0.3750 g, 51%, 2 steps). XH NMR (500 MHz, CHCl3-i/) delta ppm 0.10 (s, 3 H) 0.11 (s, 3 H) 0.91 (s, 9 H) 1.33 – 1.51 (m, 3 H) 1.80 – 1.90 (m, 1 H) 2.02 (t, J=7.7 Hz, 1 H) 2.13 (t, J=12.0 Hz, 1 H) 2.55 (dd, J=13.6, 7.3 Hz, 1 H) 2.82 (dd, J=13.2, 7.6 Hz, 1 H) 3.10 (s, 3 H) 3.76 (s, 3 H) 3.77 (s, 3 H) 4.03 (s, 3 H) 4.80 (d, J=13.2 Hz, 1 H) 4.82 (d, J=13.2 Hz, 1 H) 4.96 – 5.26 (m, 2 H) 6.12 (d, J=2.5 Hz, 1 H) 6.24 (s, 1 H) 6.32 (dd, J=8.5, 2.2 Hz, 1 H) 6.81 (d, J=8.5 Hz, 1 H) 7.04 (s, 1 H) 7.11 (s, 1 H) 13.73 (s, 1 H). LC-MS 647.5 [M+H]+, RT 1.90 min.

The synthetic route of Trimethyl methanetricarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; BRANSTROM, Arthur; JOSYULA, Vara Prasad, Venkata Nagendra; ARNOLD, Michael, Andrew; GERASYUTO, Aleksey, I.; KARP, Gary; WANG, Jiashi; WO2013/33228; (2013); A1;,
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Some common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, molecular formula is C11H13BrO2, 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. Recommanded Product: tert-Butyl 4-bromobenzoate

Example 80 [0240] A mixture of 1 ,3,4-oxathiazinane 3,3-dioxide (70 mg, 1 .30 mmol), tert-butyl 4-bromobenzoate (100 mg, 0.39 mmol), palladium acetate (9 mg, 0.04 mmol), Xantphos (34 mg, 0.06 mmol), and cesium carbonate (192 mg, 0.59 mmol) in dioxane (1 .0 ml_) in a microwave vial was degassed with argon and subjected to microwave irradiation: 100 ¡ãC for 2 hrs. The mixture was then partitioned between ethyl acetate and water, and the organic layer was dried (sodium sulfate), concentrated, and purified via silica chromatography (eluent: methanol in dichloromethane) to afford the product tert-butyl 4-(3,3-dioxido-1 ,3,4-oxathiazinan-4-yl)benzoate (121 mg, 98percent) as a white solid. 1 H-NMR (400 MHz, d6-DMSO): delta 7.93-7.91 (m, 2H), 7.46-7.44 (m, 2H), 5.00 (s, 2H), 4.08-4.06 (m, 2H), 3.94-3.92 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59247-47-1, its application will become more common.

Reference:
Patent; NANT HOLDINGS IP, LLC; TAO, Chunlin; YU, Chengzhi; ARP, Forrest; WEINGARTEN, Paul; SOON-SHIONG, Patrick; WO2014/71298; (2014); A1;,
Ester – Wikipedia,
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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. 1150566-27-0, name is Ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 1150566-27-0

A heterogeneous mixture of 2-(3-fluorophenyl)piperidine (0.1 g, 0.6 mmol), spray dried potassium fluoride (0.12 g, 2.2 mmol) and ethyl 6-chloroimidazo[1,2-b]pyridazine-3-carboxylate (I-7) (0.1 g, 0.4 mmol) in DMSO (3 mL) was heated to 100 C. for 18 hours. The mixture was poured into water, extracted with EtOAc, washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was purified by column chromatography on silica gel with DCM/MeOH gradient as eluant to yield ethyl 6-(2-(3-fluorophenyl)piperidin-1-yl)imidazo[1,2-b]pyridazine-3-carboxylate (X-156). 1H NMR (400 MHz, MeOD-d4) delta 8.17 (s, 1 H), 8.01 (d, J=10 Hz, 1H), 7.42-7.36 (m, 2H), 7.13-7.05 (m, 3H), 5.70 (s, 1H), 2.02-1.94 (m, 1 H), 1.79-1.70 (m, 1H), 1.63-1.57 (m, 2H), 1.47-1.37 (m, 1H), 1.29 (t, J=7.2 Hz, 3H). MS m/z 369.2 (M+1)+.

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; IRM LLC; US2012/65184; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 24398-88-7, name is Ethyl 3-bromobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 3-bromobenzoate

The 3-morpholinobenzoyl chloride used as a starting material was prepared as follows: A mixture of ethyl 3-bromobenzoate (1.92 ml), morpholine (1.25 ml), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.336 g), sodium tert-butoxide (1.615 g) and tris(dibenzylideneacetone)dipalladium(0) (0.33 g) and toluene (25 ml) was stirred and heated to 90 C. for 18 hours under argon. The reaction mixture was allowed to cool to ambient temperature and extracted with 1M hydrochloric acid. The aqueous phase was basified with concentrated sodium hydroxide solution and extracted with ethyl acetate. The organic phase was dried (MgSO4) and evaporated. The residual oil was purified by column chromatography on silica gel using a 47:3 mixtute of methylene chloride and methanol as eluent. There was thus obtained N-(3-morpholinobenzoyl)morpholine (0.45 g).

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; AstraZeneca AB; US6465455; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 88709-17-5, These common heterocyclic compound, 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, 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 chilled solution of diisopropylamine (67.5 ml, 0.48 mol)in THF (500 ml) a solution of n-Butyllithium in hexane (1.2 M, 300ml) was added, maintaining the temperature between -20 to -25C and stirred for l hour at ‘-15 to -25 C. After chilling the reactionmixture to about -75 C, a solution of ethyl 2-ethoxy-4-methylbenzoate (50 g, 0.24 mol) in THF (100 ml) was added,maintaining the temperature between -70 to -75 C and stirred for2.5 hours. A solution of ssoc-anhydride (57.6 g, 0.26 mol) in THF(50 ml) was added, maintaining the temperature between -70 to -75 C and stirred for l hour. After warming the reaction mixture toabout -10 C, water (500 ml) was added and stirred. The organiclayer was preserved and aqueous layer was further extracted withethyl acetate (2 x 500 ml). The extracts were combined withoriginal organic layer and combined organic phase was washedwith water and brinoe. The product was isolated by evaporating theiorganic layer underreduced pressure. Yield: 50 g, 67.5% To a chilled solution of diisopropylamine (13.5 L, 96 mol) inTHF (100 L) a solution of n-Butyllithium in hexane (1.2 M, 60 L)was added, maintaining the temperature between -20 to -25 Cand stirred for 2 hour at -15 to -25 C. After chilling the reactionmixture to about -75 C, l,3-dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone (30 L)was added followed by a solution of ethyl 2-ethoxy-4-methylbenzoate (10 Kg, 48 mol) in THF (20 L),maintaining the temperature between -70 to -75 C and stirred for3 hours. A solution of Boc-anhydride (11.5 Kg, 52 mol) in THF (10L) was added, maintaining the temperature between -70 to -75 Cand stirred for 1.5 hour. After warming the reaction mixture toabout -10 C, water (100 L) was added and stirred. The organiclayer was preserved and aqueous layer was further extracted withethyl acetate (2 x 100 L). The extracts were combined with originalorganic layer and combined organic phase was washed with waterand brine. The product was isolated by evaporating the organiclayer under reduced pressure. Yield: 12.0 Kg, 81 %To a chilled solution of diisopropylamine (67.5 ml, 0.48 mol)in THF (500 ml) a solution of n-Butyllithium in hexane (1.2 M, 300ml) was added, maintaining the temperature between -20 to -25C and stirred for l hour at -15 to -25 C. After chilling the reactiormixture to about -75 C, hexamethylphosphoramide (100 ml) wasadded followed by a solution oef ethyl 2-ethoxy-4-methylbenzoate(50 g, 0.24 mol) in THF (100 ml), maintaining the temperaturebetween -70 to -75 C and stirred for 2.5 hours. A solution of Boc-anhydride (57.6 g, 0.26 mol) in THF (50 ml) was added,maintaining the temperature between -70 to -75 C and stirred forl hour. After warming the reaction mixture to about -10 C, water(500 ml) was added and stirred. The organic layer was preservedand aqueous layer jwas further extracted with ethyl acetate (2 x500 ml). The extracts were combined with original organic layerand combined organic phase was washed with water and brine.The product was isolated by evaporating the organic layer underreduced pressure. Yield: 55 g, 74%.

The synthetic route of 88709-17-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOCON LIMITED; WO2005/19140; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 251458-15-8, These common heterocyclic compound, 251458-15-8, name is Methyl 2-(3-bromophenyl)-2-methylpropanoate, 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 82-(3 -Bromophenyl)-2-methylpropionic acidSodium hydroxide (2M, 20 mL) was added to a solution of Intermediate 7 (6.5 g) in MeOH (20 mL) and THF (20 mL). The resulting mixture was refluxed for 2 h. The mixture was evaporated, and the residue partitioned between water and DCM (100 mL each). The aqueous phase was acidified (2M hydrochloric acid) and extracted with DCM (100 mL then 50 mL). The combined organic phases were dried (MgSO4) and the solvent removed in vacuo to give the title compound (4.55 g, 68% over two steps) as a cream solid. deltaH (CDCl3) 7.54 (s, IH), 7.40 (d, IH), 7.33 (d, IH), 7.21 (t, IH), 1.59 (s, 6H).

The synthetic route of 251458-15-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB PHARMA S.A.; BUeRLI, Roland; HAUGHAN, Alan, Findlay; MACK, Stephen, Robert; PERRY, Benjamin, Garfield; RAPHY, Gilles; SAVILLE-STONES, Elizabeth, Anne; WO2010/52448; (2010); A2;,
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Application of 99548-54-6, 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. 99548-54-6 name is Methyl 3-bromo-2-methylbenzoate, This 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.

A mixture of compound 32-1 (7 g, 40 mmol), methyl 3-bromo-2-methylbenzoate (11 g, 48 mmol), K3P04 (25 g, 120 mmol), Pd2(dba)3 (915 mg, 1 mmol), X-phos (952 mg, 2 mmol) in 100 mL of dried toluene was heated under a N2 atmosphere at 100C for 18 h. Then water (200 mL) wasadded,and the mixture was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated to give the crude product. The crude product was purified by flash column chromatography on silica gel eluted with petroleum ether:ethyl acetate (3:1) to give 32-2. MS (ESI) m / e (M+H): 323.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; HAGMANN, William K.; NARGUND, Ravi P.; BLIZZARD, Timothy A.; JOSIEN, Hubert; BIJU, Purakkattle; PLUMMER, Christopher W.; DANG, Qun; LI, Bing; LIN, Linus S.; CUI, Mingxiang; HU, Bin; HAO, Jinlai; CHEN, Zhengxia; WO2014/19186; (2014); A1;,
Ester – Wikipedia,
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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. 39503-51-0, name is Methyl 5-bromo-2,4-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Methyl 5-bromo-2,4-dimethoxybenzoate

To potassium isopropylidene trifluoroborate (4.87 g, 32.7 mmol) and 5-bromo-2,4-dimethoxybenzoic acid methyl ester (7.5 g, 27.3 mmol) in THF (195 ml) was added Cs2CO3 (26.6 g, 81.8 mmol) in water (39 ml). The reaction was degassed and Pd(PPh3)4 (1.58 g, 1.36 mmol) added. The reaction was heated at reflux for three days then quenched by adding water and extracted with EtOAc (¡Á2). The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to leave an orange solid. The product was taken up in EtOAc again and the precipitate filtered. The filtrate was evaporated to dryness to yield 5-isopropenyl-2,4-dimethoxy-benzoic acid methyl ester (6.2 g). 1H NMR (Me-d3-OD) 7.68 (1H, s), 6.66 (1H, s), 5.10-5.08 (1H, m), 5.02-5.00 (1H, m), 3.93 (3H, s), 3.92 (3H, s), 3.84 (3H, s), 2.08-2.06 (3H, m). MS: [M+H]+ 237.

The synthetic route of 39503-51-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics