Author: Jessica.F

Related Products of 383-62-0, The chemical industry reduces the impact on the environment during synthesis 383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, I believe this compound will play a more active role in future production and life.

To a mixture of (2S,3R,4R,5S,6R)-2-(5-(bicyclo[4.2.0]octa-1 (6),2,4-trien- 3-ylmethyl)-4-chloro-2-hydroxyphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran- 3,4,5-triol (Compound No.8) (260 mg, 0.64 mmol) in N,N-dimethylformamide (3.0 ml) with CS2CO3 (416 mg, 1.28 mmol) was added ethyl 2-chloro-2,2- difluoroacetate (151 mg, 0.95 mmol). The reaction mixture was stirred at room temperature for overnight, then purified by chromatography on a C18 reversed phase column to yield the title compound as a white solid. 1 H NMR(400 MHz, CD3OD) delta 7.47 (s, 1H), 7.23 (s, 1H), 7.04 (d, J = 7.6 Hz, 1H), 6.93 (d, J = 7.6 Hz, 1H), 6.88 (s, 1H), 6.75 (t, J = 72.4 Hz, 1H), 4.48 (d, J = 9.6 Hz, 1H), 4.03-4.12 (m, 2 H), 3.88 (d, J = 12.0 Hz, 1H), 3.64 – 3.68 (m, 1H), 3.45 – 3.56 (m, 2 H), 3.35 – 3.42 (m, 2 H), 3.13 (s, 4 H); MS (ES) m/z: 474.1 [M+NH4]+.

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, Ethyl 2-chloro-2,2-difluoroacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 773134-11-5, name is Methyl 4-bromo-2,6-difluorobenzoate, belongs to esters-buliding-blocks compound, 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 773134-11-5, Quality Control of Methyl 4-bromo-2,6-difluorobenzoate

4-Bromo-2,6-difluoro-benzoic acid methyl ester (250 mg, 1 mmol) was dissolved intriethylamine (5 mL) and dichloropalladium(bis)triphenylphosphine (36 mg, 0.05 mmol) was added followed by copper iodide (10 mg, 0.05 mmol) and cyclopropylacetylene (85 iL, 1.2 mmol). The reaction mixture was heated for 1 hour at 100 G under microwave radiation. The mixture was cooled to room temperature and filtered through DecaliteTM and concentrated under reduced pressure. The crude residue was purified by column chromatography (heptane to ethyl acetate = 9/1 v/v%) to afford 214mg of the title compound (yield: 90.6%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; NETHERLANDS TRANSLATIONAL RESEARCH CENTER B.V.; DE MAN, Adrianus Petrus Antonius; UITDEHAAG, Joost Cornelis Marinus; STERRENBURG, Jan Gerard; DE WIT, Joeri Johannes Petrus; SEEGERS, Nicole Wilhelmina Cornelia; VAN DOORNMALEN, Antonius Maria; BUIJSMAN, Rogier Christian; ZAMAN, Guido Jenny Rudolf; (88 pag.)WO2017/153459; (2017); A1;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 57381-59-6, name is Methyl 5-bromo-2-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 5-bromo-2-fluorobenzoate

Methyl-5-benzyl-2-fluorobenzoate To a solution of methyl-5-bromo-2-fluorobenzoate (350 mg, 1 .5 mmol) in dioxane (20 ml_), was added sequentially 2-benzyl-4, 4,5, 5-tetramethyl-1 ,3, 2-dioxaborolane (327 mg, 1 .5 mmol), anhydrous potassium phosphate (955 mg, 4.5 mmol) and [1 ,1 ‘-bis(diphenylphosphino)ferrocene]palladium(ll) chloride (7 mg, 0.01 mmol) under an argon atmosphere. The mixture was stirred at 90C overnight before dioxane was concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with ethyl acetate : petroleum ether = 1 :10 to afford methyl-5-benzyl-2-fluorobenzoate (350 mg, crude) as a colorless oil, which was used directly without further purification. LCMS (ESI): m/z = 245.1 [M+H]+.

According to the analysis of related databases, 57381-59-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; X-RX DISCOVERY, INC.; RUEBSAM, Frank; WANG, Ce; NI, Haihong; MULVIHILL, Mark, J.; BABISS, Lee; RENZETTI, Louis; ZHANG, Ying; (99 pag.)WO2015/175171; (2015); A1;,
Ester – Wikipedia,
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Reference of 64113-91-3, 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 64113-91-3 as follows.

A solution of 3- (3-PHENYL-1, 2, 4-oxadiazol-5-yl) propanoic acid (0. 1G, 0. 46MMOL) in DICHLOROMETHANE (10ML) was treated with 1, 1-dimethylethyl 2-aminobenzoate (0.089g, 0. 46MMOL), 1- (3-DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE HYDROCHLORIDE (0.097g, 0. 51MMOL) and 1H-1, 2, 3-BENZOTRIAZOL-1-OL (0.075g, 0. 56MMOL). After 4 days the reaction mixture was evaporated to dryness and the residue treated with a solution of TRIFLUOROACETIC acid (1ML) in DICHLOROMETHANE (1ML). After 2 hours the mixture was evaporated to dryness and the residue dissolved in 1ml of DMSO and subjected to purification using mass-directed HPLC. The title compound, which crystallized as a white solid from the eluant upon standing for 2 days, was filtered and dried to give 0.024g (15%) of the title compound. NMR. 5H (400MHZ, D6-DMSO) ; 3.05 (t, 2H, J=7.0 Hz), 3.32 (t, 2H, J=6.8 Hz, (partially obscured by water), 7.15 (t, 1 H, J=7.5 Hz), 7.56 (m, 4H), 7.98 (m, 3H), 8.41 (d, 1 H, J=8.3 Hz), 11. 27 (s, 1 H), 13.67 (s, 1 H) ; m/z 338 [MH+].

According to the analysis of related databases, 64113-91-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/16870; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 89-71-4, The chemical industry reduces the impact on the environment during synthesis 89-71-4, name is Methyl 2-methylbenzoate, I believe this compound will play a more active role in future production and life.

(1) To 50 g of Na-X type zeolite dry powder (Zeolum type F-9; 100 meshes or finer, produced by Tosoh Corporation) was added dropwise 7.51 g (50.0 mmol) of methyl 2-methylbenzoate with stirring. Further, 3.9 ml (75 mmol) of bromine was added dropwise thereto at 45~50 C., and the mixture was stirred at 80 C. for 1 hour. To the reaction mixture was added a solution of potassium carbonate (5.5 g) in water (50 ml) and methanol (250 ml). The mixture was stirred at room temperature for 10 minutes and filtered. The residual zeolite powder was washed with warmed hydrous methanol (10%, 250 ml). The filtrate and the washing were combined and concentrated. The residue was diluted with ethyl acetate, washed twice with water, dried and concentrated. The residue (2.98 g) was subjected to silica gel column chromatography (eluted with n-hexane:toluene=10:1 and then 5:1 and then 3:1) to obtain 1.97 g (8.60 mmol) of methyl 5-bromo-2-methylbenzoate as crystals.

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, Methyl 2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sumitomo Chemical Company, Limited; US6489487; (2002); B1;,
Ester – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9BrO2

Reference Example 11 [0605] [0606] A mixture of methyl 4-bromo-3-methylbenzoate (4.58 g), [1,1?-bis(diphenylphosphino)-ferrocene]dichloropalladium (II) (1.46 g), potassium carbonate (11.0 g) and 2-(trifluoromethyl)phenylboronic acid (7.60 g) was stirred in DMF (100 mL) at 80 C. for 24 hours. After cooling to room temperature, the reaction mixture was diluted with a mixed solvent of ethyl acetate-toluene (1:1) and filtered. Water was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 11-1 (5.61 g). N-Bromosuccinimide (2.06 g) and benzoyl peroxide (133 mg) were added to a solution of compound 11-1 (3.07 g) in carbon tetrachloride (47 mL) and the mixture was heated to reflux for 6 hours. After cooling to room temperature, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 11-2 (4.05 g) as a crude product. The crude product (3.78 g) of compound 11-2 was dissolved in acetic acid (73 mL), sodium acetate (4.17 g) was added thereto, and the mixture was heated to reflux for 16 hours. After cooling to room temperature, the reaction solution was concentrated under reduced pressure to give a residue, to which water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a residue, which was purified with silica gel column chromatography (hexane/ethyl acetate) to give compound 11-3 (2.39 g). Compound 11-3 (2.04 g) was dissolved in a mixed solvent of tetrahydrofuran-methanol (1:1) (40 mL), 1N aqueous solution of sodium hydroxide (23 mL) was added dropwise thereto, and the mixture was stirred at room temperature for 25 hours. The reaction solution was acidified by addition of 2N aqueous solution of hydrochloric acid, concentrated under reduced pressure and ethyl acetate and 1N aqueous solution of hydrochloric acid were added. The organic layer was extracted, washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give a residue, which was azeotropically distilled with toluene to give compound 11-4 (1.69 g). Compound 11-5 (89 mg) was prepared from compound 11-4 (94 mg) in the same manner as the second step of Reference Example 9. Compound 11-1: 1H-NMR (CDCl3) delta 2.08 (s, 3H), 3.94 (s, 3H), 7.22 (d, J=8.1 Hz, 2H), 7.50 (t-like, J=7.6 Hz, 1H), 7.59 (t-like, J=7.1 Hz, 1H), 7.77 (d, J=7.7 Hz, 1H), 7.88 (md, J=7.9 Hz, 1H), 7.94 (m, 1H). Compound 11-2: 1H-NMR (CDCl3) delta 3.96 (s, 3H), 4.04 (d, J=10.4 Hz, 1H), 4.40 (d, J=10.4 Hz, 1H), 7.27 (d, J=8.1 Hz, 2H), 7.43 (d, J=7.3 Hz, 1H), 7.52-7.64 (m, 2H), 7.79 (d, J=7.3 Hz, 1H), 7.99 (dd, J=8.0, 1.7 Hz, 1H), 8.21 (d, J=1.7 Hz, 1H). Compound 11-3: 1H-NMR (CDCl3) delta 2.00 (s, 3H), 3.94 (s, 3H), 4.81 (AB q, JAB=22.8 Hz, 2H), 7.28 (d, J=7.9 Hz, 2H), 7.48-7.59 (m, 2H), 7.76 (d, J=7.2 Hz, 1H), 8.00 (dd, J=8.0, 1.7 Hz, 1H), 8.14 (d, J=1.3 Hz, 1H). Compound 11-4: 1H-NMR (CDCl3) delta 4.42 (AB q, JAB=23.0 Hz, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.50-7.61 (m, 2H), 7.78 (d, J=7.5 Hz, 1H), 8.05 (dd, J=8.0, 1.6 Hz, 1H), 8.34 (s, 1H). [0607] Compound 11-5: 1H-NMR (CDCl3) delta 4.83 (AB q, JAB=20.4 Hz, 2H), 7.27 (d, J=7.5 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.50-7.61 (m, 2H), 7.77 (d, J=7.2 Hz, 1H), 8.08 (dd, J=7.9, 1.8 Hz, 1H), 8.21 (d, J=1.7 Hz, 1H).

According to the analysis of related databases, 148547-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DAINIPPON SUMITOMO PHARMA CO., LTD.; Katayama, Seiji; Hori, Seiji; Hasegawa, Futoshi; Suzuki, Kuniko; US2013/116227; (2013); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 1186-73-8,Some common heterocyclic compound, 1186-73-8, name is Trimethyl methanetricarboxylate, molecular formula is C8H12O6, 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.

Step 5; methyl 9-(((tert-butyldimethylsilyl)oxy)methyl)-l-(2,4-dimethoxybenzyl)-4- hydroxy-8-methyl-2-oxo-2,5,6,8-tetrahydro-lH-indolo[6,5-h]quinoline-3- carboxylate The N-(2-(((tert-butyldimethylsilyl)oxy)methyl)- 1 -methyl-7,8-dihydro- 1H- benzo[f]indol-5(6H)-ylidene)-l-(2,4-dimethoxyphenyl)methanamine (1.40 g, 2.84 mmol) and trimethyl methanetricarboxylate (0.95 g, 5.00 mmol) were mixed together in PI12O (7.0 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) under a blanket of Argon. The reaction mixture was cooled to room temperature, then purified by column chromatography (hexanes followed by EtOAc/hexanes 25-60% gradient) to yield the product as a yellow foam (1.158 g, 63% 2 steps). XH NMR (500 MHz, CHCl3-i/) delta ppm 0.06 (s, 6 H) 0.90 (s, 9 H) 2.58 – 2.72 (m, 2 H) 2.89 (t, J=6.6 Hz, 2 H) 3.62 (s, 3 H) 3.78 (s, 3 H) 3.80 (s, 3 H) 3.97 (s, 3 H) 4.77 (s, 2 H) 5.37 (s, 2 H) 6.19 (s, 1 H) 6.42 (d, J=2.4 Hz, 1 H) 6.46 (dd, J=8.4, 2.4 Hz, 1 H) 7.14 (d, J=8.4 Hz, 1 H) 7.18 (s, 1 H) 7.63 (s, 1 H) 13.60 (s, 1 H). LC-MS 619.6 [M+H]+, RT 1.76 min.

The synthetic route of 1186-73-8 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;,
Ester – Wikipedia,
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Application of 40061-54-9, These common heterocyclic compound, 40061-54-9, name is Ethyl 2-(2-chlorophenyl)acetate, 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 35 2-(alpha-ethoxycarbonyl-2-chlorobenzylidene)-1-methylpyrrolidine Follow the procedure of Example 31 to obtain 73.8 g (93percent of theory) of the title compound (b.p. 129° to 0.008 mm of Hg) from 98.4 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate, 56.1 g of 2-chlorophenylacetic acid ethyl ester and a solution of 9.5 g of sodium in 190 ml of ethanol.

The synthetic route of 40061-54-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Byk Gulden Lomberg Chemische Fabrik G.m.b.H.; US4279918; (1981); A;,
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. 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, A new synthetic method of this compound is introduced below., SDS of cas: 35418-07-6

Example 13; Propionic Acid Ester Analogue (18) of Am-580; A solution of the compound 17 (39 mg, 0.168 mmol) in benzene (2.5 ml) was added with thionyl chloride (122 mul, 1.67 mmol) and DMF (1 drop), and the mixture was refluxed by heating for 1 hour. Volatile substances were evaporated, then the residue was added with benzene (3 ml), the solvent was evaporated again, and the residue was dried under reduced pressure. A solution of this residue in dichloromethane (1 ml) was cooled on ice, and added with a solution of methyl 3-(4-aminophenyl)propionate (36 mg, 0.201 mmol) and triethylamine (117 mul, 0.841 mmol) in dichloromethane (2 ml), and the mixture was stirred at 0 C. for 30 minutes, and at room temperature for further 16 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous sodium sulfate, and then the solvent was evaporated. The residue was purified by silica gel column chromatography (eluted with chloroform), and the residue was recrystallized to obtain the title compound 18 (55 mg, 83%) together with the recovered compound 17 (6 mg, 15%).Compound 18: colorless needles, melting point: 118.5-119.5 C. (dichloromethane-hexane)MS (m/z): 393 (M+, 15), 249 (4), 215 (100), 172 (5), 157 (10), 91 (6), 43 (9)IR (KBr) cm-1: 1731, 16381H-NMR (CDCl3) delta: 1.29 (6H, s), 1.30 (6H, s), 1.70 (4H, s), 2.61 (2H, t, J=8 Hz), 2.92 (2H, t, J=8 Hz), 3.66 (3H, s), 7.17 (2H, A2B2, J=8.5 Hz), 7.36 (1H, d, J=8 Hz), 7.55 (1H, dd, J=8, 2 Hz), 7.56 (2H, A2B2, J=8.5 Hz), 7.86 (1H, d, J=2 Hz), 7.99 (1H, br s, CONH)

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; RESEARCH FOUNDATION ITSUU LABORATORY; US2010/286427; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 101-97-3, name is Ethyl 2-phenylacetate, belongs to esters-buliding-blocks compound, 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 101-97-3, Formula: C10H12O2

(1′-Ethoxycarbonyl-1′-methyl)ethylbenzene To a solution of ethyl phenylacetate (32.8 g, 200 mmol) in THF (1000 mL) under argon was added sodium bistrimethylsilylamide (2M in THF, 100 mL). After 45 minutes. methyl iodide (13 mL) was added over 15 minutes and the mixture was stirred at rt for 30 minutes. Additional sodium bistrimethylsilylamide (2M in THF, 100 mL) was added, followed, after 30 minutes, by methyl iodide (14 mL). After 30 minutes the mixture was diluted with hexane and washed with water. The organic phase was dried, filtered and evaporated to give (1′-ethoxycarbonyl-1′-methyl)ethylbenzene (28.0 g, 146 mmol, 73%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Boehringer Ingelheim Pharmaceuticals, Inc.; US6156784; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics