Esters-buliding-blocks

Electric Literature of 6091-64-1, 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. 6091-64-1, name is Ethyl 2-bromobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Example 4 To a solution (25 ml) of 2-(4-trifluoromethylphenyl)furan (3.18 g) in tetrahydrofuran was added dropwise n-butyl lithium (1.6 M solution in hexane, 10.0 ml) under an argon atmosphere at -78C. This mixed solution was heated to room temperature, and a solution (30 ml) of zinc chloride (2.25 g) in tetrahydrofuran was added. This mixture was stirred for 1 hr., and then ethyl 2-bromobenzoate (2.38 ml) and tetrakis (triphenylphosphine)palladium (0.433 g) were added. This mixture was stirred overnight under an argon atmosphere, and then poured into 0.5 M hydrochloric acid. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1, volume ratio) to give ethyl 2-[5-(4-trifluoromethylphenyl)-2-furyl]benzoate (2.54 g, yield 47%) as a pale-yellow oil. NMR (CDCl3) delta: 1.12 (3H, t, J = 7.2 Hz), 4.27 (2H, q, J = 7.2 Hz), 6.70 (1H, d, J = 3.6 Hz), 6.87 (1H, d, J = 3.6 Hz), 7.41 (1H, dt, J = 1.4, 7.4 Hz), 7.53 (1H, dt, J = 1.4, 7.4 Hz), 7.61-7.79 (6H, m).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-bromobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1405636; (2004); A1;,
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These common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-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. SDS of cas: 99548-55-7

Example 17: 4-cyano-2-methylbenzoic acid methyl ester; To a solution of 4-bromo-2-methylbenzoic acid (108 g, 471 mmol) inLambda/,Lambda/-dimethylformamide (4 L) under a nitrogen atmosphere was added zinc (II) cyanide (88.5 g, 753.6 mmol) and tetrakis(triphenylphosphine)palladium (65 g, 56.60 mmol). The reaction mixture was stirred at 1000C for 16 hours. The reaction mixture was diluted with toluene and the phases were separated. The aqueous phase was extracted twice with toluene. The combined organic phases were washed with brine and saturated aqueous ammonium hydroxide, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate / cyclohexane 1 :5) to give 4-cyano-2- methylbenzoic acid methyl ester (73 g, 89percent yield). 1H NMR (400 MHz, CDCl3): 7.78 (d, IH), 7.52 (m, 2H), 3.92 (s, 3H), 2.62 (s, 3H) ppm.

The synthetic route of Methyl 4-bromo-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; MAIENFISCH, Peter; GODFREY, Christopher Richard Ayles; JUNG, Pierre Joseph Marcel; HUETER, Ottmar Franz; RENOLD, Peter; WO2010/127928; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, 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 1000342-11-9, category: esters-buliding-blocks

01629] Step 4: Synthesis of methyl 5-bromo-2-methyl-3-[(oxan-4-yl)amino]benzoate[01630] To a solution of methyl 3-amino-5-bromo-2-methylbenzoate (3.0 g, 12 mmol) in 1 ,2- dichloroethane (48 ml) under nitrogen, was added oxan-4-one (2.3 ml, 25 mmol) followed by acetic acid (4.2 ml, 74 mmol). The reaction mixture was stirred for 5 minutes before the addition of sodium triacetoxyborohydride (7.8 g, 37 mmol). After stirring for 64 hours, deionized water (100 ml) was added and the mixture was neutralized with solid NaHC03. The phases were separated and the aqueous layer was extracted with EtOAc (4 x 50 ml). The combined organic extracts were dried over MgS04, filtered and concentrated in-vacuo. The residue was purified by flash column chromatography (50g silica, Isolute cartridge, 10-30% EtOAc:Heptanes) to give the title compound (3.5 g 85%) as a white solid. LC-MS 99.8m/z= 327.9, 328.9, 329.9, 330.9; NMR (500 MHz, Chloroform-d) delta ppm 7.24 (d, J=1.73 Hz, 1 H) 6.85 (d, J=l .58 Hz, 1 H) 4.03 (dt, J=l 1 .82, 3.3 1 Hz, 2 H) 3.88 (s, 3 H) 3.66 (br.s., 1 H) 3.56 (td, J=U .55, 1 .97 Hz, 2 H) 3.47 – 3.55 (m, 1 H) 2.24 (s, 3 H) 2.06 (d, J= 13.56 Hz, 2 H) 1.47 – 1 .60 (m, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-amino-5-bromo-2-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; EPIZYME, INC.; EISAI CO., LTD.; KUNTZ, Kevin, Wayne; CHESWORTH, Richard; DUNCAN, Kenneth, William; KEILHACK, Heike; WARHOLIC, Natalie; KLAUS, Christine; ZHENG, Wanjun; WO2012/142513; (2012); A1;,
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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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Related Products of 110661-91-1,Some common heterocyclic compound, 110661-91-1, name is tert-Butyl 4-bromobutanoate, molecular formula is C8H15BrO2, 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.

Part A Preparation of 6-[(5-Hydroxypentyl)oxy]-2-(4-t-butoxy-4-oxobutyloxy)benzenepropanoic Acid Methyl Ester A mixture of 2-hydroxy-6-[(5-hydroxypentyl)oxy]-benzenepropanoic acid methyl ester (2.04 g, 7.23 mmol) (as described by Cohen, N. EP Appl. 531,823), t-butyl 4-bromobutyrate (1.93 g, 8.67 mmol), and K2CO3 (2.29 g, 16.6 mmol) in DMSO (60 mL) was stirred at ambient temperatures under nitrogen for 21 h. The solids were removed by filtration and the filtrate was diluted with water (100 mL), and extracted with EtOAc (3*100 mL). The combined organic extracts were washed with water and sat. NaCl, dried (MgSO4), and concentrated to give product as a yellow oil (2.98 g). A portion (487 mg) was purified by silica gel flash chromatography (40:60 EtOAc/hexanes) to give the title compound as a colorless oil (367 mg, 73.3%). 1H NMR (CDCl3): 7.08 (t, J=8.2 Hz, 1H), 6.48 (d, J=8.2 Hz, 2H), 4.00-3.89 (m, 4H), 3.70-3.62 (m, 5H), 3.04-2.93 (m, 2H), 2.50-2.39 (m, 4H), 2.11-1.99 (m, 2H), 1.88-1.75 (m, 2H), 1.72-1.52 (m, 5H), 1.43 (s, 9H); MS: m/e 447.3 [M+Na].

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-bromobutanoate, its application will become more common.

Reference:
Patent; Bristol-Myers Squibb Pharma Company; US6416733; (2002); B1;; ; Patent; Carpenter JR., Alan P.; US2003/3049; (2003); A1;; ; Patent; Barrett, John Andrew; Cheesman, Edward Hollister; Harris, Thomas David; Liu, Shuang; Rajopadhye, Milind; Sworin, Michael; US2003/124053; (2003); A1;,
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10602-03-6, name is Ethyl 4-ethynylbenzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 10602-03-6

General procedure: To a solution of 10S1 (0.10 g, 0.59 mmol), Pd(PPh3)4 (41 mg, 0.035 mmol), and CuI (34 mg,0.18 mmol) in degassed tetrahydrofuran/diisopropylamine (THF/DIPA) (5/1, v/v) (19 mL) was added2,5-diiodothiophene (DIT) (0.20 g, 0.59 mmol). The solution was stirred at 60 C for 5 h. After coolingto room temperature, the reaction mixture was diluted with dichloromethane and passed through Celiteto remove the metal catalyst. The solution was washed with 1 N HCl aqueous solution and water, andthen dried over Na2SO4. After removing the solvent by evaporation, the crude product was purified bysilica gel chromatography using hexane-dichloromethane (3/2, v/v) as the eluent to give the desiredproduct as a pale yellow solid (62 mg, 27% yield).

The synthetic route of 10602-03-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ikai, Tomoyuki; Shimizu, Sho; Kudo, Tomoya; Maeda, Katsuhiro; Kanoh, Shigeyoshi; Bulletin of the Chemical Society of Japan; vol. 90; 8; (2017); p. 910 – 918;,
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13412-12-9, name is Methyl 3-(methylamino)but-2-enoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of Methyl 3-(methylamino)but-2-enoate

General procedure: 1195 mg (9.25 mmol 1 eq.) 1 and 1000 mg (9.25 mmol 1 eq.) 1,4-benzoquinone is solved in 12 mL nitromethane. The mixture is left for 24 hrs (no stirring). Crystals of product precipitate. They were filtered, washed with nitromethane and recrystallized from EtOAc. Rf in PE+EtOAc 2+1: 0.2. Yellow solid, yield: 1300 mg, 64 %. Compound described in 2.

The synthetic route of 13412-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Schaefer, Anja; Burstein, Ethan S.; Olsson, Roger; Bioorganic and Medicinal Chemistry Letters; vol. 24; 8; (2014); p. 1944 – 1947;,
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Reference of 5941-55-9, The chemical industry reduces the impact on the environment during synthesis 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, I believe this compound will play a more active role in future production and life.

To a mixture of 5-amino-1H-pyrazole-4-carbonitrile (10.00 g, 92.51 mmol) in DMF (350.00mL) was added ethyl (E)-3-ethoxyacrylate (13.34 g, 92.51 mmol) and Cs2CO3 (60.38 g, 185.02mmol). The mixture was stirred at 100C for 2 hrs. After LCMS showed the reaction was complete, the reaction mixture was cooled to 25C, then added to water (300 mL), acidified by HC1 (1 M) till pH = 4, then filtered. The filter cake was dried in vacuum to give 5-hydroxypyrazolo[1,5- ajpyrimidine-3-carbonitrile (10.00 g, yield: 67.5 1%) as a white solid.

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 (E)-3-Ethoxyacrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BLUEPRINT MEDICINES CORPORATION; WENGLOWSKY, Steven, Mark; MIDUTURU, Chandrasekhar, V.; BIFULCO, Neil, Jr; KIM, Joseph, L.; (91 pag.)WO2017/87778; (2017); A1;,
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Synthetic Route of 24398-88-7, 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. 24398-88-7 name is Ethyl 3-bromobenzoate, 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 stirred mixture of a compound of formula V (1 eq), a boronic acid derivative of general formula VI (1.1 eq) and tetrakis(triphenylphosphine)palladium (0.03 eq) in an organic solvent (e.g. 1,2-dimethoxy-ethane) is added at room temperature aqueous 1 M sodium carbonate solution (2.5 eq), the reaction mixture is heated at 80 to 90 C. for around 18 h, cooled, poured into ice-water and extracted two times with ethyl acetate. The combined organic layers are washed two times with brine, dried (e.g. MgSO4) and evaporated. The crude product is further purified by flash chromatography on silica gel (ethyl acetate/n-heptane) and crystallization (e.g. dichloromethane/diethyl ether/n-heptane) to give compounds of general formulae Ia or Ib.Prepared from hexamethyldisilizane (16.5 mL, 79 mmol) and n-BuLi (48.4 mL, 77 mmol) in TBME (40 mL), then commercially available ethyl 3-bromobenzoate (7.55 g, 33 mmol) and tert-butyl acetate (4.86 mL, 36 mmol) in TBME (80 mL) according to the general procedure III. Obtained as a light yellow oil (9.934 g, 101%; 95% purity).

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

Reference:
Patent; Gatti McArthur, Silvia; Wichmann, Juergen; Woltering, Thomas Johannes; US2008/261957; (2008); 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. 4131-74-2, name is Dimethyl 3,3-Thiodipropionate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4131-74-2

Chemistry The preparation of target compounds 9-28 was described in Schemes 1 and 2. Compounds 7a-d and 8a-e were synthesized according to the procedures reported previously by our group [18,19]. The different substituent of phenylamine reacted with triphosgene to get compound compounds 7a-d. 8a-e was synthesized from the different substituent of chlorobenzene through three steps. The key intermediates 4-(2-chloro-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidin-4-yl)morpholine (4a) and 2-chloro-4-morpholino-7,8-dihydro-5H-thiopyrano[4,3-d]pyrimidine 6,6-dioxide(4b) were synthesized according to the procedures reported previously by our group

The synthetic route of 4131-74-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lei, Fei; Sun, Chengyu; Xu, Shan; Wang, Qinqin; Ouyang, Yiqiang; Chen, Chen; Xia, Hui; Wang, Linxiao; Zheng, Pengwu; Zhu, Wufu; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 27 – 35;,
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