Category: 59247-47-1

59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 tert-Butyl 4-bromobenzoate

(2S,3’S)-2-Methyl-[1,3′]bipyrrolidinyl dihydrochloride (8) (1.1 g, 4 mmol) was treated with NaOt-Bu (1.1 g, 2equiv) in MeOH (30 mL), filtered, and concentrated. To this flask was added tert-butyl-4-bromo-benzoate (9) (1.0 g, 3.89 mmol), sodium tert-butoxide (538 mg, 5.6 mmol), tris(dibenzylideneacetone)-dipalladium-(0) (35 mg, 0.039 mmol), BINAP (72 mg, 0.116 mmol), and toluene (40 mL) under nitrogen. The reaction flask was heated to 80 °C (external) for 24 h with stirring until the starting material was completely consumed as judged by TLC analysis. The mixture was cooled to room temperature, taken up in DCM (50 mL), filtered, and concentrated. The crude product was then purified by a silica gel flash chromatography eluted with 0-5percent of 7 N NH3/MeOH in DCM to get 1.02 g (80percent) of the title compound as a yellow oil. LCMS: RT = 2.23 min, MS: 331 (M+H+). 1H NMR (300 MHz, CDCl3) delta 7.87 (d, J = 8.7 Hz, 2H), 6.49 (d, J = 8.7 Hz, 2H), 3.6-3.23 (m, 5H), 3.01 (m, 1H), 2.78 (m, 1H), 2.55 (q, J = 8.4 Hz, 1H), 2.22-1.43 (m, 13H), 1.14 (d, J = 6.3 Hz, 3H).

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

Reference:
Article; Gao, Zhongli; Hurst, William J.; Hall, Daniel; Hartung, Ryan; Reynolds, William; Kang, Jiesheng; Nagorny, Raisa; Hendrix, James A.; George, Pascal G.; Bioorganic and Medicinal Chemistry; vol. 23; 3; (2015); p. 429 – 438;,
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Adding a certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, 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 59247-47-1, name: tert-Butyl 4-bromobenzoate

To a 50 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6-dichlorophenyl)-1H-pyrazol-5- yl]methoxy]-2-azabicyclo [2.2.1] heptane li (200 mg, 0.53 mmol, 1.00 equiv.), toluene (5 mL), Pd(OAc)2 (25 mg, 0.11 mmol, 0.20 equiv.), Xantphos (64 mg, 0.11 mmol, 0.20 equiv), Cs2CO3 (518 mg, 1.59 mmol, 3.00 equiv.), and tert-butyl 4-bromo-2-fluorobenzoate (134 mg, 0.49 mmol, 1.10 equiv.). The resulting mixture was heated at 90¡ãC overnight and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1/3) to give tert-butyl 4-[(1S,4S,5R)-5-[[4-cyclopropyl-l-(2,6- dichlorophenyl)-1H-pyrazol-5-yl]methoxy]-2-azabicyclo[2.2.1] heptan-2-yl]-2-fluorobenzoate 2a (176 mg, 58percent) as a yellow 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, tert-Butyl 4-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. Recommanded Product: tert-Butyl 4-bromobenzoate

Example 80 [0240] A mixture of 1 ,3,4-oxathiazinane 3,3-dioxide (70 mg, 1 .30 mmol), tert-butyl 4-bromobenzoate (100 mg, 0.39 mmol), palladium acetate (9 mg, 0.04 mmol), Xantphos (34 mg, 0.06 mmol), and cesium carbonate (192 mg, 0.59 mmol) in dioxane (1 .0 ml_) in a microwave vial was degassed with argon and subjected to microwave irradiation: 100 ¡ãC for 2 hrs. The mixture was then partitioned between ethyl acetate and water, and the organic layer was dried (sodium sulfate), concentrated, and purified via silica chromatography (eluent: methanol in dichloromethane) to afford the product tert-butyl 4-(3,3-dioxido-1 ,3,4-oxathiazinan-4-yl)benzoate (121 mg, 98percent) as a white solid. 1 H-NMR (400 MHz, d6-DMSO): delta 7.93-7.91 (m, 2H), 7.46-7.44 (m, 2H), 5.00 (s, 2H), 4.08-4.06 (m, 2H), 3.94-3.92 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59247-47-1, its application will become more common.

Reference:
Patent; NANT HOLDINGS IP, LLC; TAO, Chunlin; YU, Chengzhi; ARP, Forrest; WEINGARTEN, Paul; SOON-SHIONG, Patrick; WO2014/71298; (2014); A1;,
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Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-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. Recommanded Product: 59247-47-1

A 3-neck flask was charged with NaOtBu (2.85 g, 28.6 mmol) and dry THF (50 mL) under nitrogen. Tris(dibenzylideneacetone)dipalladium(0) (0.26 g, 0.28 mmol) and (S)-ToI- Binap (0.47 g, 0.69 mmol) were then added under nitrogen. After stirring for 15 min, l-(4- chlorophenyl)pentan-l-one (4.21 g, 21.0 mmol) was added, followed by tert-butyl 4- bromobenzoate (5.0 g, 19.1 mmol) under nitrogen. The mixture was heated at 600C for 8 hours. The mixture was diluted with heptane (100 mL) and poured into a solution of saturated NaHCO3 (aq) (60 mL) and ice (40 g). The resulting layers were separated, and the aqueous phase was back-extracted with methyl tert-butyl ether (50 mL). The combined organics were washed with saturated NaHCO3 (aq) then 10percent NaCl (aq). The organic solution was filtered through a bed of silica 60 (84 g, wetted with 1 :1 methyl tert-butyl ether/heptane), and washed with 1:1 methyl tert-butyl ether/heptane (600 mL). The combined filtrate was concentrated to afford an orange oil that was used directly for the next step: 1H NMR (500 MHz, CDCl3): delta 7.91 (d, J = 8.1 Hz, 2 H); 7.86 (d, J = 8.4 Hz, 2 H); 7.35 (d, J = 8.4 Hz, 2 H); 7.32 (d, J – 8.2 Hz, 2 H); 4.53 (t, J = 7.2 Hz, 1 H); 2.19-2.09 (m, 1 H); 1.85-1.76 (m, 1 H); 1.56 (s, 9 H); 1.35-1.18 (m, 2 H); 0.91 (t, J = 7.3 Hz, 3 H); LCl : 1.35 min. (M-tBu+H)+ 317.

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

Reference:
Patent; MERCK SHARP &; DOHME CORP.; LIN, Songnian; ZHANG, Fengqi; PARMEE, Emma, R.; DEWNANI, Sunita, V.; WO2010/88061; (2010); A1;,
Ester – Wikipedia,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 59247-47-1 as follows. Product Details of 59247-47-1

To a solution of tert-butyl 4-bromobenzoate (2 g, 7.8 mmol) and 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (4 g, 16 mmol) in 1,4-dioxane (30 mL) was added 1,1?-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane (0.64 g, 0.8 mmol) and potassium acetate (3.0 g, 31 mmol). The reaction mixture was stirred at 90¡ã C. under nitrogen for 12 hours. After the reaction, it was allowed to cool to room temperature and concentrated in vacuo, then diluted with ethyl acetate (100 mL), washed with water (100 mL). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, ethyl acetate/petroleum ether=1:20) to give the pure product tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.8 g, 75percent). 1H NMR (300 MHz, CDCl3): delta 7.95 (d, J=8.1 Hz, 2H), 7.83 (d, J=8.4 Hz, 2H), 1.59 (s, 9H), 1.35 (s, 12H).

According to the analysis of related databases, 59247-47-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Constellation Pharmaceuticals, Inc.; Albrecht, Brian K.; Audia, James Edmund; Cook, Andrew S.; Gagnon, Alexandre; Harmange, Jean-Christophe; Nasveschuk, Christopher G.; US9206128; (2015); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 59247-47-1, 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. 59247-47-1, name is tert-Butyl 4-bromobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a 100 mL round-bottom flask purged and maintained under an inert atmosphere of nitrogen was added (1S,4S,5R)-5-[[l-cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5- yl]methoxy]-2-azabicyclo[2.2.1]heptane 621 (45 mg, 0.12 mmol, 1.00 equiv.), toluene (20 mL), tert-butyl 4-bromobenzoate (45.7 mg, 0.18 mmol, 1.50 equiv), BINAP (15 mg, 0.02 mmol, 0.20 equiv.), Cs2CO3 (116 mg, 0.36 mmol, 3.00 equiv.), and Pd2(dba)3 (11 mg, 0.01 mmol, 0.10 equiv.). The resulting mixture was heated for at 1 10¡ãC for 2 days. After cooling to room temperature, solids were filtered out, and the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1 : 10 to 1 :5, and to 1 :3). Removal of solvents afforded tert-butyl 4-[(1S,4S,5R)-5-[[l- cyclopropyl-4-(2,6-dichlorophenyl)-1H-l,2,3-triazol-5-yl]methoxy]-2-azabicyclo[2.2.1]heptan- 2-yl]benzoate 70a (40 mg, 61percent) as a light brown oil.

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

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-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. SDS of cas: 59247-47-1

4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester To a degassed mixture of 4-(piperazin-1-yl)-benzoic acid ethyl ester (1.45g, 6.2 mmol), 4-bromobenzoic acid tert-butyl ester (1.75g, 6.8 mmol), cesium carbonate (3.9g, 12 mmol) in dioxane (25 mL) was added tris(dibenzylideneacetone)dipalladium (300 mg, 5 molpercent) and 2-(dicyclohexylphosphino)-2′,4′,6′-tris(isopropyl)-biphenyl (x-phos, 300 mg, 10 molpercent). The mixture was heated in a sealed tube with stirring at 100 ¡ãC for 3 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The crude material was purified through a flash column chromatography using ethyl acetate and hexanes to give the intermediate 4-[4-(4-ethoxycarbonylphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester as solid (1.3 g, 51 percent yield) The above intermediate, (1.2g, 2.68 mmol) was suspended in methanol (100 mL) and THF (100 mL) and sodium hydroxide solution (1N, 80 mL) was added. The mixture was refluxed for 2 hrs and then concentrated. The mixture was acidified with 1N HCl and the solid formed was filtered to give 4-[4-(4-carboxyphenyl)-piperazin-1-yl]-benzoic acid tert-butyl ester (1.1g). LCMS calcd for C22H26N204 (m/e) 382. Obsd: 381 (M-H+)

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

Reference:
Patent; Madrigal Pharmaceuticals, Inc.; BOLIN, David, R.; CHEUNG, Adrian, Wai-hing; HAMILTON, Matthew, Michael; MARCOPULOUS, Nicholas; McDERMOTT, Lee, Apostle; QIAN, Yimin; EP2350311; (2013); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 ¡ãC 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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 59247-47-1, These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-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.

INTERMEDIATE 1(R>4-[2-(4-CHLOROPHENYL)-l-PROPYLETHAN-2-ONE-l-YL]BENZOIC ACID TERT-BUTYL ESTER15 Step A. tert-Butyl 4-[2-f4-Chlorophenyl)-l-propylethan-2-one-l-yllbenzoateA 3-neck flask was charged with NaOtBu (2.85 g, 28.6 mmol) and dry THF (50 mL) under nitrogen. Tris(dibenzylideneacetone)dirhoaIladium(0) (0.26 g, 0.28 mmol) and (S)-ToI- Binap (0.47 g, 0.69 mmol) were then added under nitrogen. After stirring for 15 min, l-(4-20 chlororhohenyl)rhoentan-l-one (4.21 g, 21.0 mmol) was added, followed by tert-butyl 4- bromobenzoate (5.0 g, 19.1 mmol) under nitrogen. The mixture was heated at 6O0C for 8 hours. The mixture was diluted with heptane (100 mL) and poured into a solution of saturated NaHCO3 (aq) (60 mL) and ice (40 g). The resulting layers were separated, and the aqueous phase was back-extracted with methyl tert-butyl ether (50 mL). The combined organics were washed with25 saturated NaHCO3 (aq) then 10percent NaCl (aq). The organic solution was filtered through a bed of MRL DOB-0000Ssilica 60 (84 g, wetted with 1 : 1 methyl tert-butyl ether/heptane), and washed with 1 : 1 methyl tert-butyl ether/heptane (600 mL). The combined filtrate was concentrated to afford an orange oil that was used directly for the next step: 1H NMR (500 MHz, CDCl3): delta 7.91 (d, J – 8.1 Hz5 2 H); 7.86 (d, J = 8.4 Hz, 2 H); 7.35 (d, J = 8.4 Hz5 2 H); 7.32 (d, J = 8.2 Hz, 2 H); 4.53 (t, J = 5 7.2 Hz5 1 H); 2.19-2.09 (m, 1 H); 1.85-1.76 (m. 1 H); 1.56 (s, 9 H); 1.35-1.18 (m, 2 H); 0.91 (t, J = 7.3 Hz, 3 H); LCl: 1.35 min. (M-tBu+H) = 317.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIN, Songnian; STEVENSON, Christian, P.; PARMEE, Emma, R.; XU, Libo; LIAO, Xibin; METZGER, Edward; LIANG, Rui; ZHANG, Fengqi; STELMACH, John, E.; WO2010/30722; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics