Category: isoquinoline

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.

To a solution of 51.0 g (245.1 mmol) of 6-bromo-isoquinoline (3) in 800 ml of dichloromethane were added under mechanical stirring 90.6 g (367.6 mmol) of 3- chloro-benzenecarboperoxoic acid (70%). After stirring for 4 h at room temperature and standing overnight, saturated sodium hydrogen carbonate-solution was added until two clear layers were obtained. The dichloromethane solution was separated and washed with saturated NaCI-solution. The aqueous layers were extracted with a chloroform/isopropanol (3:1) mixture and the organic layers were combined, washed again with saturated NaCI-solution, dried over magnesium sulfate and evaporated. The obtained crude product (53,0 g) was used without further purification. Rt = 0.89 min (Method C). Detected mass: 226.2 (M+H+)., 34784-05-9

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

Reference£º
Patent; SANOFI-AVENTIS; WO2008/77552; (2008); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13130-79-5,1-Bromoisoquinolin-3-amine,as a common compound, the synthetic route is as follows.

EXAMPLE 4 1-Bromo-3-aminoisoquinoline is reacted with an equimolar quantity of morpholine as described in Example 1 to give 1-morpholinyl-3-aminoisoquinoline. Yield: 92%. M.p.: 153-154 C.

13130-79-5, The synthetic route of 13130-79-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Egyt Gyogyszervegyeszeti Gyar; US4324894; (1982); A;,
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58-74-2, 1-(3,4-Dimethoxybenzyl)-6,7-dimethoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

EXAMPLE IV 6,7-Dimethoxy-1-(alpha-morpholinomethyl)-veratrylisoquinoline dihydrochloride (P3313) A mixture of 8 g (0.024 mole) of papaverine, 0.93 g (0.031 mole) of paraformaldehyde, 2.62 g (0.030 mole) of morpholine, 2.5 ml of concentrated hydrochloric acid, and 100 ml of ethyl alcohol was stirred and heated at reflux for 8 hours. The reaction mixture was cooled at -5C for 24 hours. The cooled reaction mixture was filtered to remove 1.5 g of papaverine hydrochloride. The filtrate was evaporated to a thick residue. This was dissolved in 100 ml of water and the solution made basic by the addition of 10N sodium hydroxide solution. The basic mixture was extracted with three 100 ml portions of ether. The ether extracts were combined, dried over anhydrous magnesium sulfate and filtered. The product was precipitated from the ether solution by the addition of hydrogen chloride. The precipitated solid was collected on a filter and recrystallized twice from isopropyl alcohol to yield 4.0 g of product melting at 182-184C. The infrared spectrum was consistent with the assigned structure. Analysis – Calculated for C25 H32 Cl2 N2 O5: C, 58.70; H, 6.32; Cl, 13.86; N, 5.48. Found: C, 58.91; H, 6.30; Cl, 13.37; N, 5.34.

58-74-2, The synthetic route of 58-74-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Armour Pharmaceutical Company; US3966724; (1976); A;,
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891785-28-7, 6-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

891785-28-7, Step 1 To a cooled (0 C.), stirred suspension of C-1 (6.018 g, 26.98 mmol, 1.00 equiv.) in BMIM.BF4 (50 mL, 0.26 mol, 9.7 equiv.) was added NO.BF4 (3.90 g, 32.7 mmol, 1.21 equiv.) in several portions over 3 min. The mixture quickly changed in color from pale yellow-brown color to yellow-orange and warmed to ambient temperature with the evolution of nitrogen. After 15 min the effervescence subsided to produce a mobile yellow-orange suspension. After 60 min at RT the mixture was treated with sat’d. aq. NaHCO3, diluted with water and extracted with EtOAc. The lower of the three layers was discarded, and the upper EtOAc phase separated. The orange-brown middle layer was diluted with sufficient water to become homogeneous and again extracted with EtOAc. The combined EtOAc phases were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 6.792 g of a pale brown crystalline solid. The crude residue was absorbed onto silica gel and purified by SiO2 chromatography eluting with an EtOAc/heptane gradient (0 to 30% EtOAc) to afford 4.248 g (70%) of 6-bromo-3-fluoroisoquinoline (C-2) as a white solid. 1H NMR (400 MHz, CDCl3) delta 8.94 (s, 1H), 8.00 (s, 1H), 7.86 (d, J=8.8 Hz, 1H), 7.63 (dd, J=8.8, 1.6 Hz, 1H), 7.17 (s, 1H). LCMS: MH+226.1/228.2.

As the paragraph descriping shows that 891785-28-7 is playing an increasingly important role.

Reference£º
Patent; Genentech, Inc.; Array BioPharma Inc.; Blake, Jim; Chen, Huifen; Chicarelli, Mark; Gaudino, John; Gazzard, Lewis; Kintz, Sam; Mohr, Pete; Robarge, Kirk; Schwarz, Jacob; Zhou, Aihe; US2014/66453; (2014); A1;,
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13130-79-5, 1-Bromoisoquinolin-3-amine is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of Pd(OAc)2 (0.0403 mmol) and triphenylphosphine (0.201 mmol) in toluene (13.0 ml_) was stirred at rt under an inert atmosphere for 10 min. After that period, commercially available 3-amino-1 -bromoisoquinoline (1.34 mmol, 300 mg), anhydrous K2CO3 (2.02 mmol), and commercially available 4-methoxybenzeneboronic acid (2.69 mmol) were sequentially added. The resulting mixture was heated at 100 C in a sealed vial under an inert atmosphere overnight. After being cooled to rt, the mixture was diluted with water and extracted with EtOAc. The combined organic phases were dried over anhydrous sodium sulphate and concentrated under vacuum. The crude residue was purified by flash column chromatography over silica gel, eluting with a 7:3 petroleum ether/EtOAc mixture as the eluent to afford intermediate V (97% yield). [1H-NMR (CDC ) d (ppm): 3.89 (s, 3H), 4.48 (bs, 2H), 6.72 (s, 1 H), 7.04 (AA?XX?, 2H, JAX = 8.8 Hz, JAAVXX? = 2.5 Hz), 7.17 (ddd, 1 H, J = 8.6, 6.7, 1.2 Hz), 7.47 (ddd, 1 H, J= 8.4, 6.7, 1.2 Hz), 7.57 (d, 1 H, J = 8.4 Hz), 7.62 (AA?XX?, 2H, JAX = 8.8 Hz, JAAVXX = 2.5 Hz), 7.90 (dd, 1 H, J= 8.5, 0.8 Hz).]

13130-79-5, As the paragraph descriping shows that 13130-79-5 is playing an increasingly important role.

Reference£º
Patent; UNIVERSITA’ DI PISA; CALDERONE, Vincenzo; MINUTOLO, Filippo; TUCCINARDI, Tiziano; TESTAI, Lara; GRANCHI, Carlotta; MARTELLI, Alma; CITI, Valentina; DE LORENZO GARDINAL, Virginia; LENZI, Giulia; LEO, Francesca; MALLOGGI, Giulia; (0 pag.)WO2019/162911; (2019); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4494-18-2,1-Isoquinolinecarboxaldehyde,as a common compound, the synthetic route is as follows.

Compound 24: 4-(2-(bis(isoquinolin-1-ylmethyl)amino)ethyl)benzene-sulfonamide: A solution of 4-(2-aminoethyl)benzenesulfonamide (1.0 g, 5.0 mmol), AcOH (1.0 mL) and isoquinoline-1-carbaldehyde (2.09 g, 13.3 mmol) in DCE (50 mL) was stirred at 75 C for 30 min under nitrogen. The reaction mixture was cooled to 0 C, and treated with NaBH(OAc)3 (3.165 g, 15 mmol). The reaction mixture was stirred at room temperature for overnight and decomposed with water. The reaction mixture was extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford 4-(2-(bis(isoquinolin-1-ylmethyl)amino)ethyl)benzenesulfonamide (1.86 g, 77%). 1H NMR (400 MHz, DMSO-d6) 8.24 (d, J = 8.8 Hz, 2 H), 7.96 (d, J = 8.4 Hz, 2 H), 7.91 (d, J = 8.0 Hz, 2 H), 7.72 (t, J = 7.8 Hz, 2 H), 7.65 (d, J = 8.4 Hz, 2 H), 7.55 (t, J = 7.6 Hz, 2 H), 7.50 (d, J = 8.4 Hz, 2 H), 7.30 (d, J= 6.0 Hz, 2 H), 7.29 (s, 2 H), 4.01 (s, 4 H), 2.94 (t, J = 7.0 Hz, 2 H), 2.78 (t, J= 7.0 Hz, 2 H); MS (ESI), 483.3 (M+H)+., 4494-18-2

As the paragraph descriping shows that 4494-18-2 is playing an increasingly important role.

Reference£º
Patent; Molecular Insight Pharmaceuticals, Inc.; Babich, John W.; Zimmerman, Craig N.; Joyal, John; Maresca, Kevin P.; Marquis, John; Lu, Genliang; Wang, Jian-cheng; Hillier, Shawn; (110 pag.)EP2706057; (2016); B1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.852570-80-0,5-Bromoisoquinolin-1-amine,as a common compound, the synthetic route is as follows.,852570-80-0

General procedure: Step 1: A glass vial was charged with corresponding bromo-heteroaryl compound (0.20mmol, 1eq), potassium metabisulfite (88mg, 0.40mmol, 2eq), tetrabutylammonium bromide (70mg, 0.22mmol, 1.1eq), sodium formate (15mg, 0.22mmol, 1.1eq), palladium(II) acetate (5mg, 0.02mmol, 0.1eq), triphenylphosphine (16mg, 0.06mmol, 0.3eq), 1,10-phenanthroline (11mg, 0.06mmol, 0.3eq). After sealing, the vial was flushed with argon for 30min and the reagents were suspended in dry, degassed DMSO (1mL) and the reaction mixture was stirred for 4h at 70C. After cooling to RT N,N-Diisopropylethylamine (70muL, 0.40mmol, 2eq) and a solution of tert-butyl (E)-(2-aminoethyl)(3-(4-(pyridin-3-yl)phenyl)allyl)carbamate (63) (106mg, 0.30mmol, 1.5eq) in dry THF (1mL) were added and the reaction mixture was cooled to 0C. Subsequently a solution of N-bromosuccinimide (62mg, 0.40mmol, 2eq) in dry THF (1mL) was added and the reaction mixture was allowed to come to RT. After stirring for 1h the reaction was quenched by adding H2O (1mL) and brine (2mL). The resulting mixture was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and the solvent removed under reduced pressure. The residue was purified via flash-column-chromatography (SiO2, 0% to 5% MeOH in DCM) to yield the desired Boc-protected product, which was used directly in step 2.

852570-80-0 5-Bromoisoquinolin-1-amine 33778566, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Article; Grimm, Sebastian H.; Gagestein, Berend; Keijzer, Jordi F.; Liu, Nora; Wijdeven, Ruud H.; Lenselink, Eelke B.; Tuin, Adriaan W.; van den Nieuwendijk, Adrianus M.C.H.; van Westen, Gerard J.P.; van Boeckel, Constant A.A.; Overkleeft, Herman S.; Neefjes, Jacques; van der Stelt, Mario; Bioorganic and Medicinal Chemistry; vol. 27; 5; (2019); p. 692 – 699;,
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147497-32-3, 6-Bromo-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a round bottomed flask charged with 6-Bromo-3,4-dihydro-2H-isoquinolin-l-one (16.9 g, 74.7 mmol), cyclopropylboronic acid (9.45 g, 1.5 equiv), tricyclohexylphosphine (1.04 mg, 0.025 equiv), and K3PO4 hexahydrate (50 g, 2 equiv) in toluene (210 mL) and H2O (15 mL) was added Pd(OAc)2 (100 mg, 0.05 equiv). The combined mixture was heated for 4 h at 100 0C. The reaction mixture was cooled, filtered and washed with toluene. The organic phase was parti- tioned and washed with water and brine, dried over Na2SO4, filtered and concentrated to an oil. Addition of hexanes produced 6-Cyclopropyl-3,4-dihydro-2H-isoquinolin-l-one as a tan solid (13.6 g). MS (ESI) 187.1 (M + H)+., 147497-32-3

147497-32-3 6-Bromo-3,4-dihydroisoquinolin-1(2H)-one 21865450, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; WO2009/98144; (2009); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.679433-91-1,5-Bromo-8-methoxyisoquinoline,as a common compound, the synthetic route is as follows.,679433-91-1

5-bromo-8-methoxyisoquinoline (56 mg, 0.235 mmol), N-(6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)naphthalen-2-yl)thiophene-3-carboxamide (~100 mg), Fibercat palladium catalyst (Johnson-Matthey, 10 mg), and K2CO3 (2 M in water, 0.25 ml, 0.5 mmol) were combined in a microwave reaction vessel and 1,4-dioxane (2 ml) was added. The reaction tube was sealed and heated in the microwave (CEM microwave) at 150 Watts and 100 C for 10 minutes. The reaction was cooled to room temperature and diluted with water and dichloromethane. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified two times using the ISCO purification system (40 g column, 0 -> 5% MeOH / CH2Cl2) and one time using Varian prep HPLC (1% -95% MeCN / water with 0.1% TFA over 70 minutes) to afford title compound (5 mg, 5%) contaminated with EPO about 2 mg of the corresponding phenol. MS (ESI pos. ion) m/z: 452 (M+H). Calc’d Exact Mass for C28H22FN3O2: 451.

The synthetic route of 679433-91-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; WO2007/5668; (2007); A2;,
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1532-97-4, 4-Bromoisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Heterocycle (0.10mmol, 1 equiv)ammonium persulfate (0.20 mmol, 2equiv),[Ir{dF(CF3ppy)}2(dtbbpy)]PF6 ( 0.2 mol%),alpha-keto acids(1.0mmol10equiv)wereplaced in a dry glass tube.Then, anhydrous DMSO1mLwereinjected into the tubeby syringe under a N2 atmosphere.The solution was then stirred at roomtemperatureunder the irradiation of 15W blue LEDs strip for 12h.After completion of thereaction,then saturated Na2CO3solution was added to adjust pH to basic.Thecombined organic layer was washed with brine and then dried overanhydrousNa2SO4.The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum andethylacetate., 1532-97-4

1532-97-4 4-Bromoisoquinoline 73743, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Article; Jia, Wei; Jian, Yong; Huang, Binbin; Yang, Chao; Xia, Wujiong; Synlett; vol. 29; 14; (2018); p. 1881 – 1886;,
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