Brief introduction of 34784-05-9

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

a) 6-( 1 -piperazinyl)isoquinoline6-Bromoisoquinoline (333 mg, 1.60 1 mmol) and palladium(II) acetate (17.97 mg,0.080 mmol) were placed in a microwave vial followed by piperazine (827 mg, 9.60 mmol), sodium tert-butoxide (215 mg, 2.24 1 mmol), and p-xylene (10 mL). The vial was capped andflushed with nitrogen and tris(1,1-dimethylethyl)phosphane (1M solution in toluene, 80 uL,0.080 mmol) was injected into the vial via syringe. The reaction was stirred and heated to 120C for 1 h. The xylene was evaporated under reduced pressure and the crude product wastaken up in dichloromethane and washed with water (2x). The organic layer was filtered toremove the catalyst, dried with sodium sulfate, and evaporated under reduced pressure toafford the title product (300 mg, 88%), which was used without further purification.MS(ES)+ mle 214.2 [M+H].

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; GLAXOSMITHKLINE LLC; ADAMS, Nicholas, David; KIESOW, Terence, John; WIGGALL, Kenneth; WO2013/177253; (2013); A2;,
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Brief introduction of 34784-05-9

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[00211] 6-Vinylisoquinoline: In a 250 mL round bottom flask, 6- bromoisoquinoline (5 g, 24 mmol)(commercially available from Kalexsyn Product List Order Number 2003-005) was dissolved in dioxane (50 ml). Vinyltributylstannane (9 mL, 29 mmol) was added and the solution was degassed with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium (3 g, 2 mmol) was added in one portion. The reaction mixture was stirred for 3 hours at 1000C. The reaction mixture was adsorbed onto silica gel, and purified by flash chromatography (5-30 %, EtOAc in hexane) to provide the product (3.0 g, 80 %). LCMS (API-ES) m/z (%): 156 (M+H+).

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; WO2009/11880; (2009); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Analyzing the synthesis route of 34784-05-9

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-05-9,6-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

General procedure: 1,3-Dimethylbarbituric acid-based alkenes 1 (0.2 mmol), isoquinolines 2 (0.2 mmol) and methyl perfluoroalk-2-ynoates 3 (0.24 mmol) were stirred in MeCN (2.0 mL) at 50 C for 2 h. When methyl 4,4,4-trifluorobut-2-ynoate 3a was used as substrate, the solvent was removed under reduced pressure, DCM (1.0 mL) and silica gel (200 mesh, 0.5 g) were added. The mixture was stirred at room temperature for another 1 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel by eluting with petroleum ether / ethyl acetate (10:1) to afford the desired products 4; If methyl 4,4,5,5,5-pentafluoropent-2-ynoate 3b or methyl 4,4,5,5,6,6,6-heptafluorohex-2-ynoate 3c was served as starting material, the solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel by eluting with petroleum ether / ethyl acetate (10:1) to afford the desired products 4 and 4′.

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Article; Yu, Minhui; Wu, Yueci; Peng, Xin; Han, Jing; Chen, Jie; Kan, Yuhe; Deng, Hongmei; Shao, Min; Zhang, Hui; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 216; (2018); p. 33 – 42;,
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Simple exploration of 34784-05-9

As the paragraph descriping shows that 34784-05-9 is playing an increasingly important role.

34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 42: 6-Bromo-4-chloroisoquinoline:6-Bromoisoquinoline (Bioorg. Med. Chem. Lett. 2002, 12, 827) (200 mg) was dissolved in sulfuryl chloride (0.5 mL) and the resultant solution was stirred at 60C for 5 minutes. Sulfuryl chloride (0.5 mL) was added to the resultant solution and the mixture was further stirred for 10 minutes. A saturated aqueous sodium hydrogen carbonate solution was added to this reaction mixture and the mixture was extracted three times with ethyl acetate. The combined organic layers were washed with saturated brine and dried over anhydrous sodium sulfate and then the solvent was distilled off under reduced pressure. The resultant residue was purified by the silica gel column chromatography (hexane: ethyl acetate = 2:1) to obtain the desired compound (119 mg) as colorless powder. 1H NMR (CDCl3, 400 MHz): delta 7.78 (1H, dd, J = 8.6, 1.8 Hz), 7.88 (1H, d, J = 8.6 Hz), 8.39 (1H, d, J = 1.8 Hz), 8.61 (1H, s), 9.12 (1H, s). EIMS (+): 241 [M]+., 34784-05-9

As the paragraph descriping shows that 34784-05-9 is playing an increasingly important role.

Reference£º
Patent; Kyorin Pharmaceutical Co., Ltd.; EP2351748; (2011); A1;,
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Brief introduction of 34784-05-9

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of 6-bromoisoquinoline (208 mg, 1 mmol), bis(pinacolato)diboron (279 mg, 1.1mmol), KOAc (323 mg, 3.3 mmol) and Pd(dppf)2Ci2 (73 mg, 0.1 mmol) in DMSO (3 ml) was heated ina microwave for 10 min at 160C. The mixture was diluted with water (20 ml) and extracted with10 EtOAc (4 x 20 ml). The combined EtOAc was washed with water (15 ml) and brine (15 ml) then dried(Na2S04). The solvent was removed to give the titled compound which was used directly for nextstep.

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; LEXICON PHARMACEUTICALS, INC.; BI, Yingzhi; CARSON, Kenneth Gordon; CIANCHETTA, Giovanni; GREEN, Michael Alan; KUMI, Godwin; LIANG, Zhi; LIU, Ying Jade; MAIN, Alan; ZHANG, Yulian; ZIPP, Glenn Gregory; WO2013/134219; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Analyzing the synthesis route of 34784-05-9

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-05-9,6-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

Reference Example 1Synthesis of 6-aminoisoquinoline (Reference Compound 1)6-bromoisoquinoline that weighed 17.2 g (see WO 2008/077553), 200 mL of 28percent ammonia water and 10.8 g of copper (II) sulfate pentahydrate were put into the autoclave and tightly sealed, and the mixture was then stirred at 190¡ã C. for 6 hours.After cooling to room temperature, the reaction solution was poured into 250 mL of a 10percent aqueous sodium hydroxide solution, followed by extraction with ethyl acetate (100 mL*5).The extract was dried over anhydrous sodium sulfate, filtered, and then concentrated.The obtained crude product was suspended in dichloromethane and then filtered to obtain 10.2 g of the compound of interest as a light brown crystal (85percent).1H-NMR spectrum (CDCl3, delta ppm): 5.54 (br s, 2H), 6.58 (s, 1H), 7.00 (d, J=9.0 Hz, 1H), 7.35 (d, J=5.5 Hz, 1H), 7.75 (d, J=9.0 Hz, 1H), 8.32 (d, J=5.5 Hz, 1H), 8.98 (s, 1H)

34784-05-9, 34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; D. WESTERN THERAPEUTICS INSTITUTE, INC; US2012/35159; (2012); A1;,
Isoquinoline – Wikipedia
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New learning discoveries about 34784-05-9

The synthetic route of 34784-05-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-05-9,6-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

A round bottom flask charged with 6-bromo isoquinoline (prepared from 4-bromobenzaldehyde according to the literature: Neiko Nerenz, et al. (1998) J. Chien7. Soc. Perkin Trans. 2,437-447, 0.200 g, 0.961 mmol), 1-Boc piperazine (0.215 g, 1.15 mmol), K3PO4 (0.286 g, 1.35 mmol), (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethylamine (0.028 g, 0.072 mmol) and Pd2dba3 (0.022 g, 0.024 mmol) in dry DME (2 mL) was purged under N2 and heated at reflux for 5 hours. After cooling, the mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried and concentrated. The residue was purified by column chromatography (1: 1 hexanes/EtOAc, ) to give 4-Isoquinolin-6-yl-piperazine-1- carboxylic acid tert-butyl ester (0.210 g, 70%) as a white solid. 1H NMR (CDC13, 400 MHz) 5 9.04 (s, 1H), 8.39 (dd, J= 6.8 Hz, J= 2. 8 Hz, 1H), 7.83 (dd, J= 9.2 Hz, J= 2.8 Hz, 1H), 7.45 (d, J= 6.8 Hz, 1H), 7.32 (dd, J= 9.2 Hz, J= 2.4 Hz, 1H), 6.98 (s, 1H), 3.64 (m, 4H), 3.35 (m, 4H), 1.50 (s, 9H). LCMS (APCI+) mlz 314 [M+H] + ; Rt = 2.14 minutes., 34784-05-9

The synthetic route of 34784-05-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ARRAY BIOPHARMA INC.; WO2005/51304; (2005); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Analyzing the synthesis route of 34784-05-9

34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-05-9,6-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

1.1 6-Bromo-4-chloroisoquinoline 6-bromoisoquinoline (2 g, 9.61 mmol) in solution in sulfuryl chloride (5 mL, 61.5 mmol) was heated at 60 C. for 5 min. Another 5 mL of sulfuryl chloride were added and the reaction mixture was heated for 25 min. Sat. NaCO3 aq. solution was added to the reaction mixture and then ethyl acetate was added. The layers were separated. The aqueous layer was extracted three times with ethyl acetate and the organic layers were combined and dried over MgSO4. The crude was purified via biotage (dichloromethane/EtOH 99.9/0.01) to give the title compound (1.3 g, 56% yield). [M+H]+ 241/243/245. Rt 1.58 min (method M)., 34784-05-9

34784-05-9 6-Bromoisoquinoline 313681, aisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; Merck Patent GmbH; Cancer Research Technology, Ltd.; SCHIEMANN, Kai; BLAGG, Julian; MALLINGER, Aurelie; RINK, Christian; SEJBERG, Jimmy; HONEY, Mark; (139 pag.)US2016/16951; (2016); A1;,
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Simple exploration of 34784-05-9

34784-05-9, As the paragraph descriping shows that 34784-05-9 is playing an increasingly important role.

34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0187] 6-bromoisoquinoline (1.80g, 8.66 mmol) was dissolved in DCM (40 mL), after cooling down the reaction to 0C m-CPBA (2.30 g, 1.3 eq, 77% max) was added slowly in small portion. The reaction was warmed up to RT to become a kind of white suspension. In 4 hours, 1 OOmL DCM was added into the solution, and washed with saturated Na2C03 solution, water and brine. The separated organic layer was dried over Na2S04 and removed under the vacuum to get the yellow solid N-oxide 6-bromoisoquinoline without further purification (1.82 g, yield -93%).

34784-05-9, As the paragraph descriping shows that 34784-05-9 is playing an increasingly important role.

Reference£º
Patent; AN, Songzhu; CUREGENIX, INC.; WO2014/159733; (2014); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

New learning discoveries about 34784-05-9

The synthetic route of 34784-05-9 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-05-9,6-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

6-Bromoisoquinoline (8, 469 mg, 2.25 mmol), potassium trifluoro(vinyl)borate (755 mg, 5.64 mmol), Cs2CO3 (2.20 g, 6.76 mmol) and dichloro[1,1?-bis(di-tert-butylphosphino)ferrocene]palladium(II) (30mg, 0.05 mmol) were suspended in THF (9 mL) and H2O (1 mL). N2 was bubbled through the slurry for 5 min, which was then sealed into a microwave tube. The reaction mixture was heated to 100 C for 1 h in a microwave reactor and cooled to r.t. The mixture was filtered; the filtrate was diluted with CH2Cl2 (10 mL) and washed sequentially with H2O (10 mL) and sat. brine (10 mL). The organic layer was dried (MgSO4), filtered and evaporated to give a brown oil. The crude productwas purified by flash silica gel chromatography (eluent: gradient 5 to30% EtOAc in heptane). Pure fractions were evaporated to dryness to afford 6-vinylisoquinoline (282 mg, 81%) as a pale yellow liquid.1H NMR (400 MHz, DMSO-d6): delta = 9.28 (s, 1 H), 8.50 (d, J = 5.7 Hz, 1H), 8.10 (d, J = 8.5 Hz, 1 H), 7.95 (s, 1 H), 7.92 (dd, J = 8.5, 1.7 Hz, 1 H),7.80 (d, J = 5.7 Hz, 1 H), 6.96 (dd, J = 17.7, 11.2 Hz, 1 H), 6.12 (d, J = 17.7Hz, 1 H), 5.51 (d, J = 11.2 Hz, 1 H).MS (ES+): m/z = 156 [M + H]+.

The synthetic route of 34784-05-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Pearson, Stuart E.; Fillery, Shaun M.; Goldberg, Kristin; Demeritt, Julie E.; Eden, Jonathan; Finlayson, Jonathan; Patel, Anil; Synthesis; vol. 50; 24; (2018); p. 4963 – 4981;,
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