Tag: M.W=100-200

Electric Literature of 43088-72-8,Some common heterocyclic compound, 43088-72-8, name is 6-Methoxyisochroman-3-one, molecular formula is C10H10O3, 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: A mixture of 6-methoxyisochroman-3-one 3242 (300 mg, 1.68 mmol), amine analogues (a – g) (2.52 mmol) and AlCl3 (45.0 mg, 0.340 mmol) were combined under anhydrous conditions in a sealed tube and heated at 150 oC for 48 h. The reaction mixture was poured into aqueous 1 N HCl (5.0 mL) and extracted with EtOAc (20 mL x 2) to afford a brown residue which was purified with column chromatography (30:70 EtOAc/Hexane). 6-Methoxy-2-(4?-methylthiazol-2-yl)-1,2-dihydroisoquinolin-3(4H)-one (33a) was obtained from 32 as a pale yellow residue (162 mg, 35%), Rf 0.76 (50:50 EtOAc/Hexane). 1H NMR (300 MHz, CDCl3): deltaH 7.27-7.25 (m, 1H, ArH), 6.84-6.75 (m, 2H, ArH), 6.58 (s, 1H, thiazole-H), 5.29 (s, 2H, ArCH2N), 3.83-3.80 (m, 5H, overlapping signals-OMe and CH2), 2.33 (s, 3H, thiazole-Me). 13C NMR (75 MHz, CDCl3): deltaC 17.7 (thiazole-Me), 39.1 (ArCH2), 49.7 (ArCH2N), 55.7 (OMe), 110.0 (thiazole-CH), 112.5 (ArCH), 113.3 (ArCH), 123.7(ArCH), 127.4 (ArC), 132.8 (ArC), 147.0 (thiazole-CMe), 158.7 (thiazole-ArCN), 159.8 (C-O), 168.4 (C=O). HRMS ESI+ calcd for C14H15N2O2S [M+H]+, 275.0854, found, 275.0855.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Methoxyisochroman-3-one, its application will become more common.

Reference:
Article; Mabank, Tanya; Alexandre, Kabamba B.; Pelly, Stephen C.; Green, Ivan R.; van Otterlo, Willem A.L.; Arkivoc; vol. 2019; 4; (2019);,
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Application of 42122-75-8,Some common heterocyclic compound, 42122-75-8, name is Methyl 5-amino-2-chlorobenzoate, molecular formula is C8H8ClNO2, 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.

1.1 2-Chloro-5-phenylamino-benzoic acid methyl ester Cs2CO3 (2.79 g), palladium(II) acetate (82 mg), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (228 mg), iodobenzene (0.69 mL) and methyl-5-amino-2-chlorobenzoate (1.13 g) were placed in a flask and flushed with argon. Dioxane (18 mL) was added and the reaction mixture was heated to 100 C. for 24 h. After cooling to RT, it was diluted with Et2O, filtered over a pad of celite and the filtrate was concentrated in vacuo. The crude material was purified by CC (Hept/EtOAc 1/0 to 8/2) to give 1.18 g of the titled compound as a light yellow solid. LC-MS (A): tR=1.05 min; [M+H]+: 262.55.

The synthetic route of 42122-75-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; Hilpert, Kurt; Hubler, Francis; Murphy, Mark; Renneberg, Dorte; US2014/73651; (2014); A1;,
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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. 2475-80-1, name is Methyl 2-amino-5-methoxybenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 2475-80-1

Example 27 Synthesis scheme for the compound of formula IA2 A mixture of 6,6-dimethyl-8-oxo-3,4,5,6,7,8-hexahydro-2H-benzo[0][ l ,4]thiazine-3- carboxylate (0.54 g, 1.0 equiv) and 3 drops of DMF in dichloromethane ( l OmL) was cooled at – 10~0C. Oxalyl chloride (0.51 g, 2.0 equiv) was added dropwise into the mixture at – 10~0C, the mixture was kept at -10~0C for another 1 hour with stirring. The solution was concentrated under reduced pressure to give (R)-ethyl 8-chloro-6,6-dimethyl-3,5,6,7-tetrahydro-2H- benzo[¡ê][l ,4]thiazine-3-carboxylate as yellow oil. The residue was diluted with ethanol (1 1 niL, 20 vol), methyl 2-amino-5-methoxybenzoate (0.72 g, 2.0 equiv) was added into the (R)-ethyl 8- chloro-6,6-dimethyl-3,5,6,7-tetrahydro-2H-benzo[Z)][ l ,4]thiazine-3-carboxyIate solution, the resulting mixture was kept at 20~30C for 20 hour with stirring. The solution was concentrated under reduced pressure. The residue was purified by column chromatography (mobile phase: DCM/MeOH = 100/1-20/1) to give (¡ê)-methyl 2-((3-((2-ethoxy-2-oxoethyl)amino)-5,5- dimethylcyclohex-2-en-l -ylidene)amino)-5-methoxybenzoate.

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; ELKIMIA; ABOU-KHALIL, Elie; RAEPPEL, Stephane; RAEPPEL, Franck; WO2013/181741; (2013); A1;,
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Synthetic Route of 10602-06-9, A common heterocyclic compound, 10602-06-9, name is Methyl 3-ethynylbenzoate, molecular formula is C10H8O2, 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.

A. Under the conditions of example 5A, 9.2 g of 3-(3-hydroxy-6-iodo-2-pyridyl)-propionic acid methyl ester is reacted with 4.8 g of 3-ethinylbenzoic acid methyl ester, worked up, and the crude product is chromatographed on silica gel with hexane/0-20% ethyl acetate. 4.7 g of 3-{3-hydroxy-6-[2-(3-methoxycarbonylphenyl)-ethinyl]-2-pyridyl}-propionic acid methyl ester of melting point 125-127 C. is obtained. IR(CHCl3): 3250 (broad), 2950, 1718, 1453, 1435, 1258, 1098, 1010 cm-1.

The synthetic route of 10602-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Schering Aktiengesellschaft; US5624943; (1997); A;,
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Application of 134-20-3, These common heterocyclic compound, 134-20-3, name is Methyl 2-aminobenzoate, 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 round bottom flask was added CuBr2 (33 mmol, 7.40 g), EtOH (250 mL) and 14a (66 mmol, 10.00 g). The mixture was stirred at 35C for 2 h. Then, another portion of CuBr2 (33 mmol, 7.40 g) was added, and the mixture was continuously stirred for 1 h at 35C before being heated at reflux. After the completion of the reaction, the mixture was cooled to room temperature, and the solvent was removed under reduced pressure. To the residue was added ammonia hydroxide (170 mL, 25% w/v) with vigorous stirring. After being stirred for 3 h at room temperature, the mixture was filtered and washed with ammonia hydroxide (5 mL ¡Á3) and water (20 mL ¡Á5). The filter cake was recrystallized with MeOH (25 mL) to produce 14bb in 95% yield as white solid. Methyl 2-amino-3,5-dibromobenzoate (14bb) White solid, mp 89.9-91.6 C, 95% yield. 1H NMR (CDCl3) delta 8.00 (d, J = 2.1 Hz, 1H), 7.71 (d, J = 2.1 Hz, 1H), 6.38 (s, 2H), 3.91 (s, 3H). 13C NMR (CDCl3) delta 167.0, 146.6, 139.1, 133.1, 112.6, 111.1, 106.5, 52.2. MS (ESI): m/z calcd for C8H8Br2NO2: 307.9 [M+H]+; found: 308.1 (79Br, 79Br, 30%), 310.1 (79Br, 81Br 100%), 312.1 (81Br, 81Br 30%).

Statistics shows that Methyl 2-aminobenzoate is playing an increasingly important role. we look forward to future research findings about 134-20-3.

Reference:
Article; Zhao, Hong-Yi; Yang, Xue-Yan; Lei, Hao; Xin, Minhang; Zhang, San-Qi; Synthetic Communications; vol. 49; 11; (2019); p. 1406 – 1415;,
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Electric Literature of 4385-35-7, 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. 4385-35-7, name is 3-Isochromanone belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Methyl 2-(2-(chloromethyl)phenyl)acetate. Hydrogen chloride gas was bubbled though a solution of 3-isochromanone (1.2 g, 8.1 mmol) in methanol (30 mL) for 3 minutes. Reaction stirred at room temperature for 8 hours. Mixture was diluted with water (70 mL). Mixture was extracted with dichloromethane (2¡Á40 mL). Combined organic layers were washed with brine (20 mL). Mixture was dried (magnesium sulfate), filtered and concentrated in vacuo. Title compound was obtained as clear colorless oil in 90% yield. 1H NMR (300 MHz, CDCl3): delta=7.40-7.26 (m, 4H), 4.67 (s, 2H), 3.80 (s, 2H), 3.69 (s, 3H).

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, 3-Isochromanone, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chaturvedula, Prasad V.; Mercer, Stephen E.; Fang, Haiquan; US2006/94707; (2006); A1;,
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Reference of 103-26-4, A common heterocyclic compound, 103-26-4, name is Methyl cinnamate, molecular formula is C10H10O2, 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.

6-methyl-4-phenyl-chromen-2-one (I ; X+Z=0 ; W = CO) 2-Bromo-4-methylphenol (2.4 ml ; 19.7 MMOL), ET4NCI (2.2 g; 13.3 MOI), CY2 (Me) N (4.2 ml ; 19.7 MMOL) and Pd (OAC) 2 (59 mg; 0.26 MMOL) were added under nitrogen at room temperature to a solution of methyl cinnamate (2.1 g; 13.1 MMOL) in DIMETHYLACETAMIDE (40 ML). The reaction mixture was stirred at 959C for 48 h, then cooled and filtered on celite. The solution was diluted with Et20 and washed 3 times with H20. The organic phase was dried over NA2SO4 and the solvent was evaporated under vacuum. GC-MS showed a conversion of 94%. The raw reaction product was purified by flash chromatography. (SIO2, n-hexane: Et20 7: 3) and the fractions collected were crystallized from ET20/N-HEXANE to give pale yellow crystals (2.4 g; 77% yield).

The synthetic route of 103-26-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CONSIGLIO NAZIONALE DELLE RICERCHE; PICCOLO, Oreste; WO2005/5356; (2005); A2;,
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Ester – an overview | ScienceDirect Topics

Related Products of 58101-60-3, 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. 58101-60-3 name is Methyl 3-cyclopentenecarboxylate, 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.

To a solution of N-methylmorpholine-N-oxide (2786 mg) in H20 (7 mL) and THF (19 mL) were added potassium osmate (VI) dihydrate (43.8 mg) in tBuOH (8 mL) and methyl 3- cyclopentenecarboxylate (1500 mg) under N2. The resulting mixture was stirred at rt overnight. The reaction mixture was treated with sodium bisulphite and extracted with DCM. The org. layer was washed with brine, dried over MgS04, filtered and concentrated under reduced pressure, affording a crude orange oil (1.39 g; 73% yield) which was used directly in the next step. 1H MR (CDC13) delta: 4.15-4.27 (m, 1H); 3.95-4.11 (m, 1H); 3.67 (s, 3H); 3.07-3.25 (m, 1H); 1.87-2.32 (m, 4H).

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; CREN, Sylvaine; FRIEDLI, Astrid; HUBSCHWERLEN, Christian; RUEEDI, Georg; ZUMBRUNN, Cornelia; WO2014/170821; (2014); A1;,
Ester – Wikipedia,
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Related Products of 426-65-3, 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. 426-65-3, name is Ethyl Pentafluoropropionate, This compound has unique chemical properties. The synthetic route is as follows.

A solution of BOC protected aniline (14 g, 72 mmol) in anhydrous ether (150 mL) at -15 C. under nitrogen was treated with a solution of t-butyllithium (1.7 M in pentane, 106 mL, 183 mmol). The reaction mixture was stirred at -15 C. for 4 hrs, cooled to -78 C., and treated with ethyl pentafluoropropionate (13 mL, 88 mmol). The mixture was allowed to slowly warm to rt and brine (500 mL) was added. The organic layer was separated, dried (MgSO4), and concentrated. The residue was taken up in methylene chloride (100 mL) and treated with TFA (5 mL) at 0 C. under nitrogen. After 1.5 hrs, the solution was treated with a cold sodium bicarbonate solution (3N, 100 mL) and organic layer was separated, dried (MgSO4), and concentrated. The crude residue (5 g, 21 mmol) was then taken up in methylene chloride (80 mL) and treated with NBS (3.6 g, 20 mmol) in portions at rt under nitrogen. After 1 hr, the solution was washed with aqueous 3N sodium bicarbonate solution (3¡Á20 mL), dried (MgSO4), and concentrated to give 1-(2-amino-5-bromophenyl)-2,2,3,3,3-pentafluoropropan-1-one as a yellow solid (6 g, 25% in three steps). 1H NMR (DMSO-d6): delta 7.97 (s, 2H), 7.67 (d, J=2.3 Hz, 1H), 7.56 (dd, J=9.2, 2.2 Hz, 1H), 6.94 (d, J=9.3 Hz, 1H); MS (ESI) m/z 318/320 ([M+H]+); MS (ESI) m/z 316/318 ([M-H]-); Anal. calcd for C9H5BrF5NO: C, 33.99; H, 1.58; N, 4.40. Found: C, 34.27; H, 1.75; N, 4.22.

The chemical industry reduces the impact on the environment during synthesis Ethyl Pentafluoropropionate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wyeth; US2005/215539; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 33689-29-1,Some common heterocyclic compound, 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, molecular formula is C5H8O3, 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.

Copper (I) iodide (650 mg, 3.41 mmol) and triethylamine (3.0 mL, 22 mmol) were added to a stirred solution of methyl 1-hydroxycyclopropanecarboxylate (2.0 g, 17.22 mmol) in acetonitrile (60 mL) at rt in a sealed tube. The reaction mixture was heated to 50 C and 2-fluorosulfonyl-2,2- difluoroacetic acid (15.0 g, 84.23 mmol) was added and stirred at 50 C at 18 h, then concentrated under reduced pressure at 30 C bath temperature. To the residue water (100 mL) was added and extracted with EtOAc (2 x 150 mL). The combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated under reduced pressure at 30 C bath temperature which gave the title compound (1.1 g) as liquid. The compound was used in next step without further purification.

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

Reference:
Patent; MEDIVIR AKTIEBOLAG; ERSMARK, Karolina; KARLSTROeM, Sofia; KLASSON, Bjoern; LUNDGREN, Stina; ROSENQUIST, Asa; SALVADOR ODEN, Lourdes; (155 pag.)WO2018/226150; (2018); A1;,
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