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
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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

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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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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%).

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

The A6-1 (210mg, 1.01mmol) was dissolved in tetrahydrofuran (10mL), was added bis (pinacolato) borate (305mg, 1.20mmol), KOAc(294mg, 3.00mmol), Pd (dppf) 2Cl2 (80mg, 0.10mmol), purged with nitrogen, refluxed overnight, cooled to room temperature, suction filtered through Celite,The filtrate was spin-dried, the residue was purified by column chromatography (petroleum ether: ethyl acetate = 4: 1) to give a yellow gummy solid (270mg, 106%).

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Reference£º
Patent; Suzhou Yunxuan Pharmaceutical Co., Ltd.; Zhang, Xiaohu; (54 pag.)CN105254613; (2016); A;,
Isoquinoline – Wikipedia
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34784-05-9, 6-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

D. 1-[(3,3-Dimethyl-3-silabutoxy)methyl]-5-(6-isoquinolyl)-2-(phenylsulfonyl)imidazole. To a solution of 6-bromoisoquinoline (73 mg, 0.35 mmol) in anhydrous DMF (0.75 mL) was added copper(II) oxide (28 mg, 0.35 mmol). The mixture was purged with nitrogen, tetrakis(triphenylphosphine)palladium(0) (55 mg, 0.048 mmol) was added, and then the materials were stirred at 100 C. for 5 minutes in a sealed vial. The vial was cooled to room temperature and then a solution of 5-(1,1-dibutyl-1-stannapentyl)-1-[(3,3-dimethyl-3-silabutoxy)methyl]-2-(phenylsulfonyl)imidazole (200 mg, 0.3.19 mmol) in anhydrous DMF (0.25 mL) was added. The mixture was purged with nitrogen then the sealed reaction was stirred at 105 C. for 8 hours. The reaction was cooled to room temperature, filtered through celite, and the celite rinsed with ethyl acetate. The filtrate was diluted with water, extracted three times with dichloromethane, and the organic layers combined. The organic solution was washed with brine, dried over anhydrous magnesium sulfate, filtered, and volatiles evaporated. The material was purified by chromatography on a normal phase silica gel column with 30 to 100% ethyl acetate in hexanes. Fractions containing clean product were combined and the solvent evaporated. The material was dried under vacuum at 60 C. to provide the title compound (1.2 g, 87%). MS (ESI) m/z 466.2 [M+1]+.

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Reference£º
Patent; D’Sidocky, Neil R.; Harris, Roy L.; Hegde, Sayee G.; Hilgraf, Robert; McCarrick, Margaret A.; McKie, Jeffrey A.; Mortensen, Deborah S.; Nadolny, Lisa; Perin-Ninkovic, Sophie M.; Sapienza, John J.; Wright, Jonathan L.; US2008/242694; (2008); A1;,
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.

[00309] 6-(4-Nitro-lH-pyrazol-l-yl)isoquinoline: A mixture of 4-nitro-lH- pyrazole (510 mg, 4.51 mmol), 6-bromoisoquinoline (375 mg, 1.80 mmol)(commercially available from Gateway Chemical Technology, Inc.), tris(dibenzylideneacetone)dipalladium (0) (165 mg, 180 mumol), 2-ditert-butylphosphino- 2′,4′,6′-triisopropyl-l,r-biphenyl (153 mg, 360 mumol), and cesium carbonate (1.76 g, 5.41 mmol) in dioxane (4 mL) was heated in a sealed vial at 105C for 6 hours. The mixture was cooled to ambient temperature and partitioned between DCM (30 mL) and H2O (30 mL). The layers were separated, and the aqueous layer was extracted with DCM (2 x 20 mL) and 10% MeOH/DCM (30 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The resulting yellow solid was dissolved in DCM, evaporated onto silica gel, and purified by flash chromatography (Biotage Si 40+M, 20% to 50% acetone/hexanes) to provide 6-(4-nitro-lH-pyrazol-l-yl)isoquinoline (374 mg, 86% yield) as a white solid. LCMS (API-ES) m/z (%): 241.1 (100%, M++H); 1H NMR (300 MHz, CDCl3) delta ppm 7.76 (d, J=5.8 Hz, IH), 8.01 (dd, J=8.8, 2.2 Hz, IH), 8.14-8.23 (m, 2H), 8.36 (s, IH), 8.65 (d, J=5.8 Hz, IH), 8.83 (s, IH), 9.34 (s, IH).

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

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

 

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

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

To a degassed solution of 2-(4-fluorophenyl)-N-methyl-6-(N- methylmethylsulfonamido)-5-(3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)benzofuran-3-carboxamide (90 mg, 0.189 mmol) and 6-bromo-isoquinoline (51 mg, 0.246 mmol) in dry DMF (1.5 mL) was added Pd(dppf)Cl2 (20 mg) and K3P04 (81 mg, 0.381 mmol) under N2. The mixture was heated to 100 C for about 15 hours. The reaction mixture was cooled to room temperature and filtered. The filtrate was washed with H20, brine, dried over Na2S04, filtered and concentrated in vacuo. The residue obtained was purified using prep- TLC (PE : EtOAc = 2 : 1) to provide 2-(4-fluorophenyl)-5-(3-(isoquinolin-6-yl)phenyl)-N- methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (Compound 210, 85 mg, 93%). 1H- MR (CDC13, 400 MHz) delta 9.62 (s, 1H), 8.46 (d, J= 6.0 Hz, 1H), 8.38 (s, 1H), 8.31-8.33 (m, 1H), 8.21-8.23 (m, 1H), 8.15 (d, J= 6.0 Hz, 1H), 7.98 (s, 1H), 7.81-7.85 (m, 3H), 7.71-7.72 (m, 1H), 7.51-7.60 (m, 3H), 7.12-7.19 (m, 2H), 6.02-6.03 (m, 1H), 3.02 (s, 3H), 2.89-2.92 (m, 6H). MS (M+H)+: 580.

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

Reference£º
Patent; MERCK SHARP & DOHME CORP.; MCCOMAS, Casey Cameron; LIVERTON, Nigel J.; SOLL, Richard; LI, Peng; PENG, Xuanjia; WU, Hao; WO2011/106986; (2011); A1;,
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Isoquinoline | C9H7N – PubChem