Month: September 2021

Application of 59247-47-1,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.

To a 100 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[3-(2-chloro-6-methylphenyl)-5-cyclopropyl-1 ,2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.l]heptane ll3h (150 rng, 0.42 mmol, l.O equiv.), Tol (20 rnL),tert-butyl4-bromobenzoate (161.2 mg, 0.63 mmoL 1.50 equiv.), Cs2C03 (408 8 mg, 1.25mmol, 3.0 equiv.), BIANP (13 mg), and Pd2(dha)3 (19 mg, 0.02 mmol, 0.05 equiv.). The5 resulting mixture was stirred at 110 °C overnight Solids were filtered out. l11e illtrate wasconcentrated under vacuum to a residue which was pmified by silica gel columnchromatography eluting with ethyl acetate/petroleum ether (l: 10 to 1 :5). Removal of solventsgave tert-huty 1 4-l(l S,4S,5R)-5-U 3-(2-chloro-6-methy lpheny 1)-5-cyclopropy 1-1,2-oxazol-4-y l] rnethoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]henzoate ll4a (l 00 mg, 45percent) as a light yellow10 oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl 4-bromobenzoate, its application will become more common.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
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Reference of 24812-90-6, These common heterocyclic compound, 24812-90-6, name is Methyl 3-amino-4-methoxybenzoate, 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.

Anhydrous p-toluene sulfonic acid (20.99 g, 110.04 mmol) was melted at 120 C and 3-amino-4-methoxy benzoic acid methyl ester (10 g, 55.20 mmol) obtained in step 1 of Preparation Example 1 and 2,4-dichlorobenzonitrile (18.99 g, 110.04 mol) were added thereto and stirred at 180 C for 6 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The concentrate was dissolved in 50 % methanol and 5 % NaOCl (30 ml, 20.64 mmol) was added dropwise thereto. After 5 min, the resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent-MeOH/CDCl3=5:95, Merck, Silicagel 60) to obtain the title compound (18 g, 10.32 mmol) in a yield of 84 %. 1H NMR (CDCl3): delta 8.23 (1H, br), 7.75 (1H, d), 7.44 (1H, d), 7.36-7.26 (2H, m), 7.03 (1H, s), 6.88 (1H, d), 3.96 (3H, s), 3.76 (3H, s) MW: 318

Statistics shows that Methyl 3-amino-4-methoxybenzoate is playing an increasingly important role. we look forward to future research findings about 24812-90-6.

Reference:
Patent; CRYSTALGENOMICS, INC.; YUYU INC.; WO2004/65370; (2004); 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. 5445-17-0, name is Methyl 2-bromopropanoate, A new synthetic method of this compound is introduced below., Formula: C4H7BrO2

To a solution of E/Z mixture (5:1) of 2-propenylphenol (2.0 g, 14.9 mmol) in anhydrous DMF (30 mL) was added K2CO3 (2.68 g, 19.37 mmol) at 0 C. After stirring for 30 min at room temperature, methyl 2-bromopropionate (2.5 mL, 22.36 mmol) was added drop-wisely to the reaction mixture with a syringe. The reaction mixture was stirred for 10 h at room temperature, and poured into water (100 mL). The organic compounds were extracted with EtOAc (3 x 50 mL). The combined organic layer was washed with brine, dried (MgSO4), and concentrated under vacuum. Purification by silica gel chromatography (EtOAc/hexane=1/9, v/v) afforded the desired product as a colorless oil (3.34 g, 96%).

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:
Article; Lee, Sujin; Shin, Ju Yeon; Lee, Sang-Gi; Tetrahedron Letters; vol. 54; 7; (2013); p. 684 – 687;,
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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. 90971-88-3, name is Methyl 2-bromo-5-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 2-bromo-5-methylbenzoate

Example 15; Synthesis of 5-methyl-2-triisopropylsilanylsulfanyl-benzoic acid methyl ester (Method 15.) 2-Bromo-5-methyl-benzoic acid methyl ester (2.06 g, 9.00 mmol), tris(dibenzylideneacetone)dipalladium (0) (83 mg, 0.09 mmol), bis(2-diphenylphosphinophenyl)ether (97 mg, 0.18 mmol), sodium tert-butoxide (1.00 g, 10.4 mmol), triisopropylsilanethiol (1.37g, 7.2 mmol) and dry toluene (10 mL) are all placed in an Emrys Optimizer EXP 20 mL microwave reactor tube. The reaction vessel is sealed and subjected to microwave heating at 150 C. for 30 minutes. Upon cooling the mixture is poured onto a plug of silica and the product is eluted with ethyl acetate-heptane (2:8). This furnishes the title compound as an oil, which is used in the next step without further purification.

The synthetic route of 90971-88-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kehler, Jan; Juhl, Karsten; Norgaard, Morten Bang; US2006/287386; (2006); A1;,
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Electric Literature of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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 solution of MeCN (1 mmol) containing chromene diene 13 (0.5 mmol) and the corresponding enamino ester 9 or? -enaminokone 11 (0.6 mmol) shown in Table 1 3.0 mL) was stirred at room temperature while adding indium (III) trifluoromethanesulfonate [Indium (III) trifluoromethanesulfonate].The reaction mixture was stirred for 2-8 hours, and after completion of the reaction was confirmed by TLC (hexane-EtOAc, 4: 1, v / v), 10 mL of water was added and the solution was extracted with ethyl acetate (10 mL x 3) .The solvent was evaporated and the residue was subjected to silica gel column chromatography using hexane-ethyl acetate (4: 1, v / v) to obtain the following compound.

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

Reference:
Patent; Yeungnam University Industry-Academic Cooperation Foundation; Lee Yong-rok; (31 pag.)KR2018/3669; (2018); A;,
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Electric Literature of 17449-48-8,Some common heterocyclic compound, 17449-48-8, name is Dimethyl 5-fluoroisophthalate, molecular formula is C10H9FO4, 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.

Concentrated [HC1] (30 ml) was added to a cooled [(-5C)] suspension of dimethyl 5-amino isophthalate (20 g, 95.6 mmol) in water (75 ml), followed by portionwise addition of [NAN02] (7.5 g, 109 mmol). The reaction mixture was then stirred for 15 min. , after which [HBF4 (18] ml, 100 mmol, 48% aqueous solution) was added. The resulting mixture was stirred at [0C] for 30 min. and the precipitate formed was collected by filtration and washed with cold methanol (60 ml) and ether (60 ml). The residue was then decomposed by heating in an oil bath [(~110C).] The cooled mixture was then diluted with ether, concentrated onto silica gel and purified by flash chromatography with 5% ethyl acetate hexane as eluant giving 9.0 g (44%) of product as a white fluffy [SOLID. LH NE (CDC13), 6] [(PPM)] : 8.57 (s, 1H), 7.95 (d, 2H), 3.97 (s, 6H). A suspension of 5-fluoro-isophthalic acid dimethyl ester (1.7 g, 8. 0 mmol) in methanol (41 ml) was treated with 1.0 N sodium hydroxide (7.2 ml, 7.2 mmol). The reaction was left stirring overnight at room temperature. After the solution was concentrated, the residue was dissolved in water and transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3 times) and then acidified with 1.0 N [HC1] to pH 2. Ethyl acetate was used to extract the precipitate, which was then washed with brine and dried over anhydrous sodium sulphate. After removal of solvent in vacuo, a total of 1.3 g (83%) of 5-fluoro-isophthalic acid monomethyl ester was isolated as a white [SOLID. LH] NMR (DMSO), [5] (ppm): 8.31 (t, 1H), 7.96 (m, 2H), 3.91 (s, 3H). Triethylamine (2.2 ml, 16.0 mmol) and isobutyl [CHLOROFORMATE] (1.0 ml, 8. 0 mmol) were added to an ice-cooled solution [OF 5-FLUORO-ISOPHTHALIC] acid monomethyl ester (1.3 g, 6.7 mmol) in dichloromethane (20 ml) and then warmed to room temperature. After stirring for 2 h, the reaction mixture was filtered and concentrated. The residue was re-dissolved tetrahydrofuran (10 ml) and then sodium borohydride [(1.] 1 g, 29.02 mmol) in water (3ml) was added drop-wise. After 1 h, the reaction was quenched with methanol and then diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Flash column chromatography on silica gel using 30% ethyl acetate in hexanes afforded 667 mg (54%) of 3-fluoro-5-hydroxymethyl-benzoic acid methyl ester as a colorless [OIL. 1H] NMR [(CDC13),] [8] (ppm): 7.82 (s, 1H), 7.63 (d, 1H), 7.32 (d, 1H), 4.76 (s, 2H), 3.93 (s, 3H). Ethanol (2 ml) was added to round bottom flask containing 3-fluoro-5-hydroxymethyl- benzoic acid methyl ester (667 mg, 3.6 mmol) and palladium (10 wt. % on activated carbon, 300 mg) under argon. The flask was evacuated using a water aspirator and then filled with hydrogen from a balloon. After stirring for 2 h, the palladium on carbon was removed by filtration through celite. The filtrate was then concentrated to afford 520 mg (87%) of 3-fluoro-5-methyl-benzoic acid methyl [ESTER. LH] NMR [(CDC13),] 8 (ppm): 7.65 (s, 1H), 7.51 (d, 1H), 7.08 (d, 1H), 3.91 (s, 3H), 2.40 (s, 3H). 0.5 N Lithium hydroxide (7.4 ml, 3.7 mmol) was added to a solution 3-fluoro-5-methyl- benzoic acid methyl ester (520 mg, 3.1 mmol) in tetrahydrofuran (7.4 ml). The reaction was stirred at [75 C] for 2 h and then the solvent was removed in vacuo. The residue was dissolved in a small amount of water and then acidified (pH about 2) by the addition of 10% [HC1] (aq. ). Following extraction of the aqueous layer with ethyl acetate, the organic layer was then washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 469 mg (98%) [OF 3-FLUORO-5-METHYL-BENZOIC] acid as a white solid. 1H NMR (DMSO), d (ppm): 7.62 (s, 1H), 7.45 (d, 1H), 7.32 (d, 1H), 2.38 (s, 3H).

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

Reference:
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
Ester – Wikipedia,
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These common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-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. HPLC of Formula: C5H9BrO2

To a solution of CH3ONa (587.78 mg, 10.88 mmol, 1.0 eq) in MeOH (20.0 mL) was addedmethyl 2-bromo-2-methyl-propanoate (1.97 g, 10.88 mmol, 1.41 mL, 1.0 eq) and tert-butyl Nhydroxy-N-methyl-carbamate (1.60 g, 10.88 mmol, 1.0 eq) at 15 C. The mixture was heated to 60 C with stirring for 16 h. TLC (PE: EtOAc = 5:1) showed that starting material was consumed completely and one main new spot formed. The mixture was evaporated to removethe solvent and get the residue. The residue was purified by column chromatography (5i02,Petroleum ether/Ethyl acetate=l0/l to 20/1) to obtain the title 0 (2.30 g, 9.30 mmol,85.49% yield) as off-white liquid. ?H NIVIR (4001V11{z, CHLOROFORM-d) = 3.74 (s, 3 H),3.11 (s, 3 H), 1.48 (d,J=4.9Hz, 15 H).

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

Reference:
Patent; NOVIRA THERAPEUTICS, INC.; KUDUK, Scott; HARTMAN, George, D.; (433 pag.)WO2018/5881; (2018); 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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

To available thiophen-3-ylamine 2p1 (0.50 g, 5.04 rnmol) was added imidate2g2 (1.08g, 5.5mmol) in ethanol (10 mL) under a N2 atmosphere. The mixture wasstirred at R.T. for 3 h at which point the reaction was concentrated. To the residuewas added ether, and the suspension filtered and washed with ether to afford adduct2p2(1.0g, 82percent). This material was sufficiently clean to be used in the subsequentstep. MS: 242.1 (MH)+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4891-38-7, name is Methyl Phenylpropiolate, 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 4891-38-7, category: esters-buliding-blocks

General procedure: A reaction kettle (30 mL) was charged with aniline (1.0 mmol), and alkyne ester (1.0 mmol). The mixture was stirred at room temperature for 10 minutes, then added terminal alkyne (1.2 mmol, 1.2 eq), AgOTf (5 mol%, 12.9 mg), HOTf (10 mol%, 15 mg), MeOH (2 mL) in the mixture. The mixture was stirred at 120 oC for 24 hours, the mixture was quenched by sat. aq. NaHCO3, and diluted with 20 mL of dichloromethane and washed with 10 mL of H2O. The aqueous layer was extracted twice with dichloromethane (10 mL) and the combined organic phase was dried over Na2SO4. After evaporation of the solvents, the residue was purified by silica gel chromatography (hexane/AcOEt = 5:1) to afford quinoline derivatives. All other compounds are synthesized in a similar manner, with the yields listed in the main text calculated from the isolated, pure products.

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

Reference:
Article; Li, Yunlan; Zhang, Qiurui; Xu, Xuefeng; Zhang, Xu; Yang, Yurong; Yi, Wei; Tetrahedron Letters; vol. 60; 14; (2019); p. 965 – 970;,
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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. 40637-56-7, name is Dimethyl 2-allylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C8H12O4

According to a reported procedure,18 a solution of dimethyl 2-allylmalonate (19) (1.77 mL, 11.0mmol, 1.0 equiv) in Et2O (25 mL) was added dropwise to a suspension of LiAlH4 (1.25 g, 33.0mmol, 3.0 equiv) in Et2O (31 mL) at 0C. The resulting mixture was stirred at room temperature for3 h; it was then cooled back to 0C and the reaction was quenched by slow addition of water (1.05mL). The mixture was allowed to warm to rt and treated with aqueous NaOH (15%, 1.05 mL) andwater (3.2 mL). The resulting white slurry was filtered through Celite and then washed with EtOAc(4 x 50 mL). After removal of the solvent by distillation under reduced pressure, the crude productwas purified by column chromatography (SiO2, eluting with Et2O) to afford diol 20 as a colorlessoil (744 mg, 6.40 mmol, 58% yield). Following a reported procedure,19 a solution of diol 20 (581 mg, 5.00 mmol, 1.0 equiv) in THF (4.0mL) was added dropwise to a suspension of NaH (60% dispersion in mineral oil, 120 mg, 5.00mmol, 1.0 equiv) in THF (10 mL). The mixture was stirred at rt for 50 min and then a solution oftriisopropyl silyl chloride (0.96 mL, 4.5 mmol, 0.9 equiv) in THF (4.0 mL) was slowly added. Afterstirring for 2 h, the reaction was quenched by treatment with aqueous K2CO3 (1.0 M, 15 mL). Theaqueous layer was separated from the organic one and extracted with Et2O (3 x 15 mL). Thecombined organic layers were washed with brine (15 mL), dried over MgSO4, filtered and thesolvent was removed in vacuo. Purification by column chromatography (SiO2, eluting with 95:5pentane:EtOAc) afforded the monoprotected diol 21 as a colorless oil (1.15 g, 4.23 mmol, 85%yield).

The synthetic route of 40637-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nicolai, Stefano; Swallow, Peter; Waser, Jerome; Tetrahedron; vol. 71; 35; (2015); p. 5959 – 5964;,
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