Month: June 2021

Some common heterocyclic compound, 2557-13-3, name is Methyl 3-(trifluoromethyl)benzoate, molecular formula is C9H7F3O2, 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: Methyl 3-(trifluoromethyl)benzoate

EXAMPLES 24 AND 25(3-(3-(Trifluoromethyl)phenyl)-4,5-dihydronaphtho[l,2-c]isoxazol-7-yl)methanol (24) andl-((3-(3-(Trifluoromethyl)phenyl)-4,5-dihydronaphtho[l,2-c]isoxazol-7- -3-carboxylic acid (25)[00331] To 6-vinyl-3,4-dihydronaphthalen-l(2H)-one oxime (Intermediate 1, 0.151 g, 0.808 mmol) was added 5 mL of toluene and the contents were concentrated under reduced pressure. The resulting solid was kept under high vacuum for 10 min. The white solid was cooled to 0 C and lithium diisopropylamide (2.0 M, 0.8 mL, 1.61 mmol) was added drop wise over a period of 3 min. The reaction mixture was stirred at 0 C for 20 min., then methyl 3-(trifluoromethyl)benzoate (0.087 mL, 0.539 mmol) was added dropwise over a period of 1 min. at 0 C. After 10 min. at 0C, concentrated sulfuric acid (0.2 mL) was added dropwise at 0 C and the reaction was stirred for 20 minutes. Water (2 mL) was added and the homogenous solution was heated at 60 C for ~2 hr. The reaction mixture was stirred overnight at room temperature. The contents were concentrated under reduced pressure. Next, 5 mL of dioxane was added and the contents were heated at 100 C for 1.5 hr. The reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate (20 mL) and sat. aq. sodium bicarbonate (10 mL). The ethyl acetate layer was dried over sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane/ethyl acetate). Fractions corresponding to the product were collected and concentrated to yield 3-(3-(trifluoromethyl)phenyl)-7-vinyl-4,5-dihydronaphtho[l,2-c]isoxazole (0.15 g, 0.439 mmol, 82 % yield) as a pale yellow solid. LC/MS M+1 = 342.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2557-13-3, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DHAR, T.G. Murali; XIAO, Hai-Yun; WATTERSON, Scott Hunter; KO, Soo S.; DYCKMAN, Alaric J.; LANGEVINE, Charles M.; DAS, Jagabandhu; CHERNEY, Robert J.; WO2011/59784; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 541-16-2, A common heterocyclic compound, 541-16-2, name is Di-tert-Butyl malonate, molecular formula is C11H20O4, 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.

Step 1: Preparation of 2-ethylcyclopropane-1,1-dicarboxylic acid di-tert-butyl ester, shown below To a suspension of benzyltriethylammonium chloride (21.0 g, 92.2 mmol) in a 50% aqueous NaOH solution (92.4 g in 185 mL H2O) was added 1,2-dibromobutane (30.0 g, 138.9 mmol) and di-tert-butylmalonate (20.0 g, 92.5 mmol). The reaction mixture was vigorously stirred for 18 hours at room temperature and treated with a mixture of ice and water. The crude product was extracted with dichloromethane (3*) and sequentially washed with water (3*), and brine. The organic extracts were combined, dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by flash column chromatography (100g SiO2, 3% diethyl ether in hexane) to provide the desired product (18.3 g, 67.8 mmol, 73% yield) which was used directly in the next reaction.

The synthetic route of 541-16-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/304626; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 6279-86-3, name is Triethyl 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. Computed Properties of C10H16O6

10129] 14.5 parts (62.4 mmol) of triethyl carboxymalonate,11.4 parts (76.4 mmol) of 5-amino-2-benzimidazolinone and0.138 part (0.626 mmol) of 2,6-di-tert-butyl-p-cresol weredissolved in 141 parts (1.93 mol) of N,N-dimethylformamide, and reacted under heating and stirring at 800 C. for 6hours. After the reaction, N,N-dimethylformamide was distilled away under reduced pressure, and 300 parts (16.7 mol) of water was added to the obtained residue. The deposit was filtered to thereby obtain the intermediate (4).

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

Reference:
Patent; CANON KABUSHIKI KAISHA; CANON FINETECH INC.; Kubo, Haruko; Ueno, Suzuka; Chizuwa, Junko; Yamamoto, Tomoya; Itabashi, Hitoshi; Terui, Yuhei; Yoshida, Yu; Murai, Yasuaki; Toyoda, Takayuki; (26 pag.)US2016/130233; (2016); 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. 13831-03-3, name is tert-Butyl propiolate, A new synthetic method of this compound is introduced below., Computed Properties of C7H10O2

To the mixture of methyl 3-iodobenzoate (157 mg, 0.60 mmol), potassium carbonate (166mg, 1.20 mmol), cupper(I) iodide (14 mg, 0.07 mmol) and PdC12(Ph3P)2 (21 mg, 0.03 mmol) in tetrahydroffiran (2 mE) was added tert-butyl propiolate (330 pL, 2.40 mmol) at room temperature. Afier stirred for 20 h at 60 C., the mixture was evaporated to dryness. Theresidue was chromatographed on a silica gel (EtOAc:hex- anes=0: 1 -1 :10) to give the title compound 9-1(155 mg, 99%yield) as a light brown oil.?H NMR (300 MHz, CDC13) oe 8.25 (t, J=1.4, 1H), 8.16- 8.05 (m, 1H), 7.80-7.68 (m, 1H), 7.46 (t, J=7.8, 1H), 3.93 (s,3H), 1.55 (s, 9H).

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; The Broad Institute, Inc.; Massachusetts General Hospital; Hung, Deborah; Stanley, Sarah; Kawate, Tomohiko; Iwase, Noriakie; Shimizu, Motohisa; (32 pag.)US9416121; (2016); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 3618-04-0, The chemical industry reduces the impact on the environment during synthesis 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, I believe this compound will play a more active role in future production and life.

EXAMPLE 5 5-Butyl-9-[1-(4,6-dimethyl-pyrimidine-5-carbonyl)-4-methyl-piperidin-4-yl]-3-(trans-4-hydroxy-cyclohexylmethyl)-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one (I-4) 4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38)-To a solution of 4-oxy-cyclohexanecarboxylic acid ethyl ester (CASRN 17159-80-7, 1.7 g, 0.01 mol) in DMF (14 mL) was added DMAP (58 mg, 0.47 mmol), TEA (1.54 mL) and tert-butyl-dimethylsilyl chloride (1.65 g, 0.011 mol). The reaction mixture was stirred at RT for 18 h, poured into ice (10 g), extracted with EtOAc (3*50 mL). The organic extracts were dried (MgSO4) filtered and concentrated. The residue was purified by SiO2 chromatography eluding with EtOAc/hexane (1:20) to afford 2.25 g (79%) of 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester (38) as colorless oil.

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, trans-Ethyl 4-hydroxycyclohexanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rotstein, David Mark; Melville, Chris Richard; US2008/249087; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 52727-57-8, These common heterocyclic compound, 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, 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 88:Methyl 2-amino-5-[4-(methylsulfonyImethyl)-6-morpholin-4-yl-pyrimidin-2- yljbenzoateA mixture of methyl-2-amino-5-bromobenzoate (250 mg), potassium acetate (320 mg) and bis(pinacolato)diboron (332 mg) in 1,4-dioxane (10 mL) was degassed for 5 minutes. 1,1′- Bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (54 mg) was added and the reaction was heated to 8O0C for 2.5 hours. 2-Chloro-4-(methylsulfonylmethyl)-6-mophiholin-4-yl-pyrimidine (381 mg), ethanol (0.75 mL), a 2M solution of sodium carbonate (2.7 mL) and additional 1,1′- bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (54 mg) were added and the heating was continued for a further 3.5 hours. The cooled reaction mixture was loaded on a SCX-2 (10 g), removed with 7N ammonia in methanol and the solution concentrated in vacuo. The residue was chromatographed on silica, eluting with 50% ethyl acetate in DCM, to give the desired material as a yellow solid (82 mg). Mass Spectrum; MH+ 407 NMR Spectrum: 1H NMR (DMSO-d6) 53.22 (3H, s), 3.69 (4H, s), 3.73 (4H, s), 3.84 (3H, s), 4.49 (2H, s), 6.77 (IH, s), 6.87 (IH, d), 7.05 (2H, s), 8.24 (IH, d), 8.79 (IH, s)

The synthetic route of 52727-57-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2007/80382; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 676621-95-7,Some common heterocyclic compound, 676621-95-7, name is Ethyl 3-(4-fluorophenyl)-2,2-dimethylpropanoate, molecular formula is C13H17FO2, 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.

Preparation of3- (4-fluorophenyl)-2, 2- dimethylpropionic acid A mixture of 3- (4-fluorophenyl)-2, 2-dimethylpropionic acid ethyl ester (10.0 g, 44.6 mmol, see Part 1 of Example 25a) and a solution of sodium hydroxide (25 g) in water (110 mL) was heated at refluxfor 18 h and cooled to room temperature. The solution was stirred on an ice bath and acidified with, concentrated aqueous hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and dried under vacuum. The residue was stirred with dichloromethane and filtered, and the filtrate was concentrated to provide an off-white solid (7.60 g, 87%). OH NMR (300 mHz, CDC13) 6 7.14 (m, 2H), 6.98 (t, J = 9 Hz, 2H), 2.88 (s, 2H), 1.22 (s, 6H); mass spec (ES-) m/z 195.2 (100%,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 Ethyl 3-(4-fluorophenyl)-2,2-dimethylpropanoate, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2005/48932; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 921222-14-2, 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. 921222-14-2 name is Ethyl 2,3-diamino-6-(methylthio)benzoate, 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 2,3-diamino-6-methylsulfanyl-benzoic acid ethyl ester (150 mg) in acetonitrile (10 mL) are added 2,3-dichlorophenyl isothiocyanate (98 muL). The reaction mixture obtained is stirred 1 hour at RT and N-(3-dimethylaminopropyl)-N’-ethylcarbodiimide hydro-chloride (EDCI, 166 mg) is added. The mixture obtained is cooled to RT, quenched with H2O and extracted with EtOAc. The organic layers obtained are combined, dried over MgSO4, filtrated and solvent is evaporated to afford the title compound (LC/MS Rt=3.55, [M]+=395.93 and 397.89 and 399.89).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2,3-diamino-6-(methylthio)benzoate, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/9774; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 618-89-3, name is Methyl 3-bromobenzoate, molecular formula is C8H7BrO2, 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: Methyl 3-bromobenzoate

In a 25 mL round-bottomed flask, toluene (10 mL) was degassed with argon for 20 min. Under a flow of argon, Pd(OAc)2 (0.05 g, 0.23 mmol), BINAP (0.23 g, 0.37 mmol) and Cs2CO3 (2.12 mmol, 6.51 mmol) were added and left to stir for a further 20 min. To the mixture, methyl (3-bromobenzoate) 1 (1.01 g, 4.65 mmol) and aniline 2 (0.51 mL, 5.58 mmol) were added. The reaction was stirred at 120 C and monitored by thin layer chromatography (TLC) for 24 h. Upon completion, the reaction was cooled to room temperature and filtered through Celite, with hexane as the eluent, followed by concentration under reduced pressure. The residue was purified by flash column chromatography on silica eluting with hexane/ethyl acetate (90:10) (Rf 0.23) to afford 0.87 g (82%) of 3 as a pale yellow solid; M.p. 110-112 C (literature M.p. 110-111 C) [40]; 1H NMR (400 MHz/CDCl3)/ppm, delta = 3.90 (s, 3H,-COOCH3), 5.81 (s, 1H, -NH), 6.98 (app. t, 1H, app J = 8 Hz, CHparaC4H4-NH), 7.09 (app. d, 2H, CHparaC2H2metaC2H2ortho-NH), 7.23 (m, 1H, HN-CH-C(COOCH3)-CHCHCH-), 7.29 (m, 3H, C2H2ortho-HN-CH-C(COOCH3)-CHCHCH-), 7.57 (app. d, 1H, HN-CH-C(COOCH3)-CH), 7.72 (m, 1H, HN-CHC(COOCH3)); 13C NMR (100 MHz/CDCl3)/ppm, delta = 52.2, 118.2, 118.4, 121.5, 121.77, 121.80, 129.4, 129.3, 131.4, 142.4, 143.6, 167.1; Found [M+H]+ (C14H14NO2) m/z 228.1019 (Calc. 228.1025); IR (ATR) v/cm-1: 3358, 3030, 1694, 1578, 1294, 744.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 618-89-3, its application will become more common.

Reference:
Article; Higgins, Clare L.; Filip, Sorin V.; Afsar, Ashfaq; Hayes, Wayne; Tetrahedron; vol. 75; 51; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 114312-57-1, A common heterocyclic compound, 114312-57-1, name is Ethyl 3-fluoro-2-methylbenzoate, molecular formula is C10H11FO2, 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.

Add ethyl 3-fluoro-2-methylbenzoate (5.1g, 28mmol) to the reaction flask,N-bromosuccinimide (5.6g, 31mmol),Benzoyl peroxide (0.34g, 1.4mmol) and CCl4 (30mL).Under the protection of nitrogen, the temperature of the reaction solution was raised to 82C and the reaction was stirred for 17 hours.After the reaction was completed, the reaction solution was cooled to room temperature, filtered, and the filter cake was washed with EtOAc (50 mL). The resulting filtrate was sequentially saturated sodium thiosulfate solution (100 mL×2),The citric acid solution (50 mL) and saturated brine (50 mL) were washed, dried over anhydrous sodium sulfate, filtered, and the filtrate was vortexed under reduced pressure.The obtained crude product was purified using silica gel column chromatography (eluent: PE/EA (v/v) = 10/1),The title compound was obtained as a light yellow oil (6.17g, 84%).

The synthetic route of 114312-57-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Luo Huichao; Ren Qingyun; Yin Junjun; Wu Chunlin; Fan Yuxin; Mo Yufeng; Zhang Yingjun; (102 pag.)CN111057074; (2020); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics