Tag: M.W=200-300

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.

Step A: tert-Butyl 4-(1-cyano-2-methoxy-2-oxoethyl)benzoate. To a mixture of Na3PO4 (9.84 g, 60.0 mmol), methyl cyanoacetate (2.38 g, 24.0 mmol), and tert-butyl 4-bromobenzoate (5.14 g, 20.0 mmol) were added Pd(dba)2 (575 mg, 1.00 mmol), toluene (60 mL), and P(t-Bu)3 (10percent wt in hexanes, 11.56 mL, 3.89 mmol). After degassing for 20 minutes, the reaction was stirred at 80¡ã C. for 16 h. The resulting mixture was diluted with EtOAc, washed with H2O and brine, dried (MgSO4), and concentrated. Flash chromatography on silica gel (0-15percent EtOAc/hexanes) gave tert-butyl 4-(1-cyano-2-methoxy-2-oxoethyl)benzoate as a white solid. 1H NMR (CDCl3) delta8.02 (d, J=7.9 Hz, 2H), 7.51 (d, J=8.2 Hz, 2H), 4.79 (s, 1H), 3.79 (s, 3H), 1.58 (s, 9H). MS (ESI) calcd [M+H]+ 276.1, found 276.1.

The synthetic route of 59247-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Grimm, Jonathan B.; Hubbs, Jed L.; Miller, Thomas; Otte, Karin M.; Siliphaivanh, Phieng; Stanton, Matthew G.; Wilson, Kevin; Witter, David; Zhou, Hua; US2009/69250; (2009); 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. 110661-91-1, name is tert-Butyl 4-bromobutanoate, A new synthetic method of this compound is introduced below., name: tert-Butyl 4-bromobutanoate

Step 1: Synthesis of ethyl 3-((1-(1-(4-(tert-butoxy)-4-oxobutyl)- 1H-pyrazol-4-yl)-6-chloro-2- cyclopropyl-7-fluoro- 1H-indol-3-yl)thio)-2-fluorobenzoate (2):1003731 To a stirred solution of indole 1 (Example 11, Step 3; 200 mg, 0.42 mmol) in DMF (5 mL) under inert atmosphere were added Cs2CO3 (206 mg, 0.63 mmol) and tert-butyl 4- bromobutanoate (141 mg, 0.63 mmol) at RT and stirred for 16 h. The mixture was diluted with ice cold water (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried (Na2504), filtered and concentrated under reduced pressure to obtain the crude. This was purified (silica gel chromatography; 20% EtOAc/ hexanes) to afford compound 2 (180 mg, 70%) as a pale brown oil. 1H NMR (400 MHz, CDC13): 5 7.67 (s, 1H), 7.64 (s, 1H), 7.63-7.60 (m, 1H), 7.18 (d,J= 8.4 Hz, 1H), 7.10-7.06 (m, 1H), 6.93 (t,J 8.0 Hz, 1H), 6.77 (t,J 7.6 Hz, 1H), 4.41 (q, 2H), 4.28 (t,J= 6.8 Hz, 2H), 2.28-2.19 (m, 4H), 1.74-1.66 (m, 1H), 1.46 (s, 9H),1.41 (t, J= 7.2 Hz, 3H), 1.06-1.02 (m, 2H), 0.89-0.84 (m, 2H); LC-MS (ES): m/z 618.6 (M + Hj.

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; PHARMAKEA, INC.; HUTCHINSON, John, Edward; LONERGAN, David; WO2015/77503; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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 69812-51-7, Safety of Methyl 4-chlorosulfonylbenzoate

Under Ar protection,Compound 26b (0.7 g, 2.98 mmol), 100 mL of dichloromethane,Morpholine (0.31mL, 3.58mmol),Et3N (1.24 mL, 8.94 mmol) was placed in a 250 mL round-bottomed flask and reacted overnight at room temperature. The reaction was detected by TLC the next day.The organic phase was sequentially washed with a 1 mol / L hydrochloric acid aqueous solution and a saturated saline solution.Dry over anhydrous Na2SO4. Concentrated under reduced pressure to obtain Intermediate 27b, 0.78 g of a white solid, with a yield of 91.2%.

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 4-chlorosulfonylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Huang Haihong; Li Gang; Wang Pengxu; (55 pag.)CN110759889; (2020); A;,
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Some common heterocyclic compound, 939-18-4, name is 3-Bromo-2H-chromen-2-one, molecular formula is C9H5BrO2, 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. name: 3-Bromo-2H-chromen-2-one

Step 2: 3-({3-[4-(isoquinolin-1 -yl)piperazin-1 -yl]propyl}amino)-2H-chromen- 2-one hydrochloride (87) A mixture of intermediates 31 b (50 mg, 0.185 mmoles, 1 eq.) and 87a (50 mg, 0.222 mmoles, 1 .2 eq.), Pd(OAc)2 (5 mg, 0.019 mmoles, 0.1 eq.), Xantphos (1 1 mg, 0.019 mmoles, 0.1 eq.) and Cs2C03 (90 mg, 0.28 mmoles, 1 .5 eq.) in 1 ,4-dioxane (2.5 ml_) was heated to 130C in a sealed tube under microwave irradiation for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue was chromatographed on silica gel (SNAP25) eluting with a gradient of 0-2% mixture A in dichloromethane, where mixture A is MeOH/NH4OH 10:1 . The partially pure product was further purified by preparative LC-MS to give 20 mg of a yellow gum. The product was dissolved in dichloromethane (4 mL) and treated with 1 M HCI solution in diethyl ether (0.16 mL) causing precipitation. The resulting mixture was evaporated under reduced pressure and the residue was triturated with diethyl ether. The solids were dried to give 24 mg of 3-({3-[4-(isoquinolin-1 – yl)piperazin-1 -yl]propyl}amino)-2H-chromen-2-one hydrochloride 87 (Y=27%). LC-MS (M-H+) = 415.3. 1 H NMR (400MHz, DMSO-d6) delta = 1 1 .1 6 (br. s., 1 H), 8.19 (d, J=7.5 Hz, 1 H), 8.08 (d, J=5.8 Hz, 1 H), 8.00 (d, J=7.5 Hz, 1 H), 7.85 (t, J=6.5 Hz, 1 H), 7.70 (t, J=7.3 Hz, 1 H), 7.57 (d, J=5.3 Hz, 1 H), 7.47 (br. s., 1 H), 7.37 – 7.10 (m, 3H), 6.68 (s, 1 H), 6.27 (br. s., 1 H), 4.00 (d, J=12.3 Hz, 2H), 4.37 – 3.81 (m, 1 H), 3.64 (d, J=1 1 .0 Hz, 4H), 3.40 (d, J=9.3 Hz, 2H), 3.28 (d, J=5.8 Hz, 4H), 2.1 1 (br. quin, J=7.0 Hz, 2H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-18-4, its application will become more common.

Reference:
Patent; AZIENDE CHIMICHE RIUNITE ANGELINI FRANCESCO A.C.R.A.F. S.P.A.; OMBRATO, Rosella; GAROFALO, Barbara; MANGANO, Giorgina; CAPEZZONE DE JOANNON, Alessandra; CORSO, Gaia; MAGARO’, Gabriele; FURLOTTI, Guido; IACOANGELI, Tommaso; (108 pag.)WO2016/96631; (2016); A1;,
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Some common heterocyclic compound, 65868-63-5, name is tert-Butyl 6-bromohexanoate, molecular formula is C10H19BrO2, 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: tert-Butyl 6-bromohexanoate

To a stirred mixture of alcohol 32 (49.7 mg, 0.10 mmol) and TBAI (3.7 mg,0.01 mmol) in DMF (1 mL) at rt was NaH (4.4 mg, 60% dispersion in mineraloil, 0.11 mmol). After 30 minutes, tert-butyl bromohexanoate (25.1 mg, 0.1mmol) was added and the solution was stirred for a further 16 h at rt. H2O (1mL) was then added, and the mixture was extracted with ether (3 ¡Á 2 mL), driedover MgSO4, filtered and concentrated in vacuo. The resultant crude oil was purified by flashchromatography (EtOAc-hexanes 1:3) giving the product as a pale oil (10 mg, 17%). vmax(neat)/cm-12856, 1727, 1367, 1104, 845; deltaH (400 MHz; CDCl3), 7.41 (d, J = 2.0 Hz), 7.32 (dt, J = 8.3, 1.7, 2H),7.27 (m, 2H), 7.03 (dt, J = 8.5, 2.0, 2H), 3.60 (t, J = 6.8, 2H) 3.47 (q, J = 6.4, 2H), 2.87 (t, J = 4.8, 4H),2.66 (t, J = 7.1, 2H), 2.37 (s, 3H), 2.20 (m, 4H), 1.75 (m, 4H), 1.60 (m, 6H), 1.44 (s, 9H); HRMS (ESI+)[M + H]+ 667.2817 calcd for C36H45Cl2N4O4 667.2812.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65868-63-5, its application will become more common.

Reference:
Article; Grant, Phillip S.; Kahlcke, Nils; Govindpani, Karan; Hunter, Morag; MacDonald, Christa; Brimble, Margaret A.; Glass, Michelle; Furkert, Daniel P.; Bioorganic and Medicinal Chemistry Letters; vol. 29; 21; (2019);,
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Application of 1000342-11-9,Some common heterocyclic compound, 1000342-11-9, name is Methyl 3-amino-5-bromo-2-methylbenzoate, molecular formula is C9H10BrNO2, 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.

01035] Step 4: methyl 3-bromo-5-(cyclopentylamino)benzoate[01036] To a stirred solution of ethyl 3-amino-5-bromobenzoate (2 g, 8.73 mmol) and cyclopentanone (2.2 g, 26.1 mmol) in methanol (20 mL), acetic acid (1.04 g, 17.4 mmol) was added and reaction stirred at room temperature for 3 h. Then sodium cyanoborohydride (1.37 21.83 mmol) was added and reaction stirred overnight. On completion, solvent was removed under reduced pressure and crude material was purified by column chromatography to afford desired compound ( 1 .6 g, 61 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-amino-5-bromo-2-methylbenzoate, its application will become more common.

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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Synthetic Route of 79669-50-4,Some common heterocyclic compound, 79669-50-4, name is methyl 5-bromo-2-methyl-benzoate, molecular formula is C9H9BrO2, 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 methyl 5-fluoro-2-methylbenzoate (0.5 g, 3.0 mmol),NBS (0.18 g, 3.0 mmol), and di-benzoyl peroxide (BPO) (36 mg, 0.15 mmol) in 1,2-dichloroethane (5 mL) was heated at 80 C for 12 huntil all starting material was consumed. The reaction was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give a crude product (0.65 g, 89%), which was used in the next step reaction without further purification.

The synthetic route of 79669-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Junli; Deng, Xiaoyan; Zhou, Siru; Wang, Na; Qin, Yujun; Meng, Liuwei; Li, Guobao; Xiong, Yuhua; Fan, Yating; Guo, Ling; Lan, Danni; Xing, Junhao; Jiang, Weizhe; Li, Qing; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 644 – 654;,
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Electric Literature of 653-92-9, 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. 653-92-9, name is Methyl 2-bromo-4-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

Methyl 2-bromo-4-fluorobenzoate (3 g), EXAMPLE 1B (4.43 g), and K2CO3 (3.56 g) were stirred in DMSO (35 mL) at 125 C. for 24 hours. The mixture was cooled, taken up in ethyl acetate (500 mL), washed with water and brine, dried over Na2SO4, filtered and concentrated. The concentrate was chromatographed on silica gel with 5-25% ethyl acetate/hexanes.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-bromo-4-fluorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ABBOTT LABORATORIES; US2010/160322; (2010); A1;,
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Application of 7459-46-3,Some common heterocyclic compound, 7459-46-3, name is Triethyl ethane-1,1,2-tricarboxylate, molecular formula is C11H18O6, 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 reflux solution of triethyl 1,1,2-ethane tricarboxylate (32) (5.0 g, 20.3 mmol) and sodium borohydride (2.3 g, 60.9 mmol) in tert-butyl alcohol (40 mL), methanol (2.5 mL) was added in the reaction mixture in three aliquots over 0.5 h. The resulting solution was heated under reflux condition for additional 0.5 h and allowed to cool down to room temperature. 1 N HCl was added with care until the solution was neutral. The solution was filtered and filtrate was extracted with ethanol. The residue was purified by silica gel column chromatography (chloroform:methanol = 7:1) to give 33 (2.1 g). Yield: 88percent; 1H NMR (300 MHz, CDCl3) delta (ppm) 3.80 (m, 6H), 1.93 (q, J = 5.4 Hz, 1H), 1.71 (m, 2H); ESI [M + H] = 121.3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Triethyl ethane-1,1,2-tricarboxylate, its application will become more common.

Reference:
Article; You, Hyun; Youn, Hyung-Seop; Im, Isak; Bae, Man-Ho; Lee, Sang-Kook; Ko, Hyojin; Eom, Soo Hyun; Kim, Yong-Chul; European Journal of Medicinal Chemistry; vol. 46; 4; (2011); p. 1153 – 1164;,
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69812-51-7, name is Methyl 4-chlorosulfonylbenzoate, 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: Methyl 4-chlorosulfonylbenzoate

Step J1 -2: methyl 6-(benzyloxy)-N-{ [4-(methoxycarbonyl)phenyl]sulfonyl}-L-norleucinate. To a solution of methyl 6-(ben2yloxy)-L-norleucinate hydrochloride (15 g, 52.1 mmol) in DCM (261 mL) was added triethylamine (15.98 mL, 115 mmol) followed by 4- carbomethoxy-phenylsulfonyl chloride (12.48 g, 53.2 mmol) by portions. After 15 minutes of stirring at room temperature, the reaction mixture was concentrated in vacuo to 1/3 volume, diluted with EtOAc, washed with 10% KHSO4, saturated aqueous NaHCtheta3, and then brine, and then dried over sodium sulfate and concentrated in vacuo to give the desired product as a crude solid. MS M+l = 450.

The synthetic route of 69812-51-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/42093; (2009); A1;,
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