Category: isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.19493-45-9,3-Chloroisoquinoline,as a common compound, the synthetic route is as follows.

To a stirred solution of crude step-c product (17 g, 0.104 mol) in concentrated sulfuric acid (10 mL) was added pottasium nitrate (11 g, 0.109 mol) in concentrated sulfuric acid solution slowly at -15 0C in 30 minutes. It was allowed to stir for 12 hours. After complete conversion the reaction mixture was poured into crushed ice. A yellow precipitate came out which was filtered and washed with water (3 x 50 mL). The solid was dried under vacuum at 80 0C to afford 20 crude compound.

19493-45-9, As the paragraph descriping shows that 19493-45-9 is playing an increasingly important role.

Reference£º
Patent; GRUeNENTHAL GMBH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; SCHIENE, Klaus; DE VRY, Jean; DAMANN, Nils; FRORMANN, Sven; LESCH, Bernhard; LEE, Jeewoo; KIM, Yong-Soo; KIM, Myeong-Seop; WO2010/127855; (2010); A1;,
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.82827-09-6,6-Bromoisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

82827-09-6, General procedure: Aryl halide (1 equiv), bis-pinacolato-diboron (1.5-3 equiv), Pd(dppf)Cl2 (0.05-0.1 equiv), and KOAc (3-6 eq.) were suspended in DMF (2-6 mL). The mixture was then heated at 90 C for 2-6 h, cooled to rt, diluted with H2O (10 mL) and extracted with EtOAc (3 ¡Á 5 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo. The residue was purified by chromatography using a stepped gradient of 0-10% EtOAc in heptane to yield the desired boronic ester.

82827-09-6 6-Bromoisoquinolin-1(2H)-one 15885182, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Article; Niculescu-Duvaz, Dan; Niculescu-Duvaz, Ion; Suijkerbuijk, Bart M.J.M.; Menard, Delphine; Zambon, Alfonso; Davies, Lawrence; Pons, Jean-Francois; Whittaker, Steven; Marais, Richard; Springer, Caroline J.; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1284 – 1304;,
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3336-43-4, 1-Chloroisoquinolin-4-ol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1 To a stirring solution of NaH (0.334 g, 8.35 mmol) in DMF (10 mL) at 0 C. was added 1-chloroisoquinolin-4-ol (1 g, 5.57 mmol). The mixture was stirred at 0 C. for 10 min. before the addition of allyl bromide (0.808 g, 6.68 mmol) dropwise. The reaction mixture was stirred at rt for 1 h. The reaction mixture was diluted with ethyl acetate and then quenched with 1N HCl solution. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated to get the crude material. The material was purified by flash chromatography with 20% of EtOAc/hexane to afford 4-(allyloxy)-1-chloroisoquinoline (1.0 g, 4.55 mmol, 83% yield) as a white solid. MS: MS m/z 220.1 (M++1).

3336-43-4, As the paragraph descriping shows that 3336-43-4 is playing an increasingly important role.

Reference£º
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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1198-30-7, 1-Isoquinolinecarbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1198-30-7, Example A13 Synthesis of (4-butylphenyl)(1-isoquinolyl)ketone Under a nitrogen atmosphere, 1-bromo-4-butylbenzene (2.29 ml, 13.0 mmol) was added to a mixed solution of magnesium (338 mg, 13.9 mmol) and tetrahydrofuran (6.5 ml), and as an initiator, catalytic amount of 1,2-dibromoethane was added, and this was stirred under reflux for 10 minutes. The solution was cooled to 0C, a tetrahydrofuran solution of 1-isoquinolinecarbonitrile (1.0g, 6.49 mmol) was added, and was stirred for another 1 hour at room temperature, and at 70C for 3 hours. Subsequently, the solution was cooled again to 0C, concentrated hydrochloric acid (2.56 ml) and methanol (11 ml) were added, and then refluxed for 2 hours. The concentrated residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was divided, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 1.72 g of the title compound. 1H-NMR(CDCl3) delta (ppm):0.93(3H, t), 1.32-1.43(2H, m), 1.58-1.66(2H, m), 2.68(2H, t), 7.28(2H, d), 7.61(1H, td), 7.74(1H, td), 7.80(1H, d), 7.87(2H, d), 7.92(1H, d), 8.20(1H, d), 8.60(1H, d)

As the paragraph descriping shows that 1198-30-7 is playing an increasingly important role.

Reference£º
Patent; Eisai Co., Ltd.; EP1300464; (2003); A1;,
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1082674-24-5, 6-Bromoisoquinoline-1-carbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Into a 2L 3-neck round bottom flask equipped with a mechanical stirrer, reflux condenser and thermocouple with heating mantle was placed 2-methyltetrahydrofuran (2-MeTHF) (10 mL/g; 8.15 moles; 817 mL; 702 g) followed by racemic-2,2′- bis(diphenylphosphino)-1 , 1 ‘-binaphthyl (BINAP) (0.04 equiv (molar); 14.0 mmol; 8.74 g) and bis(dibenzylideneacetone)palladium (Pd2(dba)3) (0.04 equiv (molar); 14.0 mmol; 8.07 g). The mixture was degassed by pulling vacuum and refilling with nitrogen three times then heated to 75 C for 15 minutes and cooled to ambient temperature. In a separate flask, (S)-3-amino-2-methylpropan-1 -ol (1.60 equiv; 561 mmol; 50.0 g, prepared using literature methods for example as disclosed in EP-A-0,089,139 published on 21 st September 1983) was dissolved in 2-methyltetrahydrofuran (5 mL/g; 4.08 moles; 409 mL; 351 g) and degassed by pulling vacuum and refilling with nitrogen three times. Into the pot containing the catalyst was added 6-(bromoisoquinoline-1 – carbonitrile) (1.00 equiv; 351 mmol; 81.75 g) and cesium carbonate (1.6 equiv (molar); 561 mmol; 185 g) in single portions followed by the solution of the aminoalcohol via addition funnel. The reaction mixture was again degassed by pulling vacuum and refilling with nitrogen three times. The reaction was heated to 70 C for 3 hours. The reaction was cooled to ambient temperature and filtered through a pad of Celite. The contents of the flask were rinsed out with three 100 mL portions of 2- methyltetrahydrofuran. The filtrate was transferred into a 2L round bottom flask equipped with a thermocouple and mechanical stirrer under nitrogen. Silica Gel (Silicylate SiliaMet Thiol) (0.4 g/g-pure-LR; 544 mmol; 32.7 g) was charged and the flask was stirred at 40 C overnight. The following morning, the reaction was cooled to < 30 C and filtered again through Celite. The pad was washed with 100mL of 2- methyltetrahydrofuran (or until no yellow color persisted in the filtrate). The filtrate was placed into a 3L round bottom flask equipped with a magnetic stir bar, distillation head (with condenser and receiving flask), and thermocouple. The mixture was heated to 60 C and placed under vacuum (-450-500 mbar) to distil out 1.3 L total of 2- methyltetrahydrofuran. 500 mL of toluene was added to precipitate the desired product. The heating mantle was removed and the reaction was allowed to reach ambient temperature. The mixture was stirred for 1 hour at ambient temperature and then the solids were collected by vacuum filtration on a sintered glass funnel. The cake was dried overnight on the funnel under vacuum. The following morning, the solids were transferred into an amber bottle and weighed (71.9 g; 298 mmol). The product was used in the next step without further purification., 1082674-24-5

As the paragraph descriping shows that 1082674-24-5 is playing an increasingly important role.

Reference£º
Patent; PFIZER INC.; CHEKLER, Eugene Lvovich Piatnitski; GILBERT, Adam Matthew; UNWALLA, Rayomand Jal; VERHOEST, Patrick Robert; ANDERSON, James Thomas; WO2015/181676; (2015); A1;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.18881-17-9,(S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol,as a common compound, the synthetic route is as follows.,18881-17-9

To a solution of 4-benzyloxy-5-methoxy-2-nitrobenzoic acid (9) (10.0 g, 33.0 mmol) in DCM (100 mL) added HATU (16.3 g, 42.9 mmol) and DIEA (8.61 mL, 49.5 mmol). The mixture was stirred at 22 C for 15 min, then added (S)-(1,2,3,4- tetrahydroisoquinolin-3-y])methanol (6.46 g, 39.6 mmol). The resulting mixture was stirred at 22 C for 2 hr, under Ar, then MeOH (50 mL) was added and the resulting precipitate was filtered and washed with DCM (100 mL). The resulting filtrate was concentrated and purified via column chromatography (25?85% EtOAc in hexane) to afford impure 10 (15.3 g 34.1 mmol) as a yellow foam. 1H NMR (500 MHz, CDCl3) (contains rotamers and impurities) delta: 8.67 (d, J= 4.6 Hz, 0.3H), 8,43 (d, J= 8.5 Hz, 0.3H), 7,85-7.82 (m, 2H), 7.79 (s, 0.3H ), 7,50 (t, J= 5.4 Hz, 5H), 7.46-7.43 (m, 4H), 7.40-7.38 (m, 2H), 7.26-7.22 (m, 2H), 7.19-7.16 (m, IH), 7.11-7.06 (m, 0.3H), 6.87 (d, ./ 7.0 Hz, IH), 6.75 (d l. ./ 1.8, 0.5 Hz, 0.3H), 6.67 (s, 1H). 5.62-5.52 (m, 1H), 5 ,26 (s, 21 1). 5.25-5 ,25 (m, H), 5.11 (s, 0.3H), 4,98-4.96 (m, 1H). 4.46-4.41 (m, IH), 4.34 (d, J= 15.4 Hz, 1H), 4.28-4.23 (m, IH), 4.03 (s, 2H), 3.97 (s, 3H), 3.93-3.91 (m, 3H), 3.80-3.75 (m, IH), 3.68-3.62 (m, 1H), 3.49-3.48 (m, IH), 3.28-3.22 (m, 0.3H), 3.19- 3.10 (m, IH), 3 ,08-3,03 (m, 1H), 2.82 (s, 14H). LC/MS: retention time = 3.15 min. (ESI) C25H25N2O6: [M+H]+ 449; found 449.

18881-17-9 (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol 776757, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; CELLERANT THERAPEUTICS, INC.; JUNUTULA, Jagath R.; SMITH, Sean W.; BORKIN, Dmitry; DEGRADO, Sylvia; GHONE, Sanjeevani; (144 pag.)WO2018/71455; (2018); A1;,
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Isoquinoline | C9H7N – PubChem

164148-92-9, tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

First 1,2,3,4- tetrahydroisoquinolin-6-amine bis hydrochloride was prepared from tert-butyl 6-amino-3,4- dihydroisoquinoline-2(1H)-carboxylate. A suspension of tert-butyl 6-amino-3,4- dihydroisoquinoline-2(1H)-carboxylate (200 mg, 0.81 mmol) in HCl (2 mL, 4 M, in dioxane, 8 mmol) was stirred at room temperature for 15 h. The mixture was concentrated and residual HCl removed by co-evaporation ethyl acetate (2 ¡Á 4 mL) to provide 1,2,3,4-tetrahydroisoquinolin-6- amine bis-hydrochloride as a pale yellow solid (176 mg, 99%) and used without further purification.

164148-92-9, As the paragraph descriping shows that 164148-92-9 is playing an increasingly important role.

Reference£º
Patent; H. LEE MOFFITT CANCER CENTER & RESEARCH INSTITUTE, INC.; BURNETTE, Pearlie; LAWRENCE, Harshani; LAWRENCE, Nicholas J.; (285 pag.)WO2017/161119; (2017); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

106778-42-1, Isoquinoline-6-carbonitrile is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation Example G-1. Isoquinoline-6-carboxylic acid A solution prepared by adding (4-bromobenzylydene)-(2,2-diethoxyethyl) amine (synthesized from 4-bromobenzaldehyde, according to the method described in J. Org. Chem., vol. 48, 3344-3346 (1983)) (51.4g, 0.189mmol) to an ice-cold concentrated sulfuric acid (20g) was added to a solution prepared by adding diphosphorus pentoxide (40g) to an ice-cold concentrated sulfuric acid (360g), and the solution was stirred at 160C for 2 hours. The reaction solution was gradually cooled to 0C, the solution was filtered through Celite pad, the filtrate was neutralized with sodium carbonate. This solution was further filtrated through Celite pad, this filtrate was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 6-bromoisoquinoline (482mg, 1.2%) was obtained as an orange oil. Next, to a solution of 6-bromoisoquinoline (382mg, 1.84mmol) in N,N-dimethylformamide (3.8mL) were added zinc cyanide (431 mg, 3.67mmol) and tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) under nitrogen atmosphere, and the mixture was stirred at 100C for 1 hour. Tetrakis(triphenylphosphine)palladium(0) (42mg, 0.0367mmol) was further added, and the mixture was stirred for 2.5 hours at 100C. The reaction mixture was allowed to room temperature, ethyl acetate and water were added for extraction, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (hexane : ethyl acetate), and isoquinoline-6-carbonitrile (234mg, 83%) was obtained as a yellow solid. Lastly, isoquinoline-6-carbonitrile (51mg, 0.331 mmol) was dissolved in diethyleneglycol (1.0mL), potassium hydroxide (9mg, 0.166mmol) was added thereto, followed by stirring at 160C for 3 hours. The reaction mixture was allowed to room temperature, neutralized using hydrochloric acid, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, then, the solvent was evaporated. Water was added to the residue, the precipitated solid was collected, washed with water, dried in vacuo, so as to obtain the title compound (12mg, 21 %) as a yellow solid., 106778-42-1

As the paragraph descriping shows that 106778-42-1 is playing an increasingly important role.

Reference£º
Patent; Eisai R&D Management Co., Ltd.; EP1782811; (2007); A1;,
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.90806-58-9,5-Methoxyisoquinoline,as a common compound, the synthetic route is as follows.,90806-58-9

To a stirred solution of Cap-138, step a (2.34 g, 14.7 mmol) in anhydrous dichloromethane (50 mL) at room temperature was added meto-chloroperbenzoic acid (77%, 3.42 g, 19.8 mmol) in one portion. After being stirred for 20 h, powdered potassium carbonate (2.0 g) was added and the mixture was stirred for 1 h at room temperature before it was filtered and concentrated to afford Cap-138, step b as a pale, yellow solid which was sufficiently pure to carry forward (2.15 g, 83.3%). XH NMR (CDC13, 400 MHz) delta 8.73 (d, J= 1.5 Hz, 1H), 8.1 1 (dd, J = 7.3, 1.7 Hz, 1H), 8.04 (d, J=7.1 Hz, 1H), 7.52 (t, J= 8.1 Hz, 1H), 7.28 (d, J = 8.3 Hz, 1H), 6.91 (d, J = 7.8 Hz, 1H), 4.00 (s, 3H); Rt = 0.92 min, (Cond.-Dl); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ Ci0Hi0NO2: 176.07; found: 176.0.

The synthetic route of 90806-58-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; LAVOIE, Rico; BENDER, John A.; ROMINE, Jeffrey Lee; RUEDIGER, Edward H.; BACHAND, Carol; LOPEZ, Omar D.; CHEN, Qi; BELEMA, Makonen; KADOW, John F.; HAMANN, Lawrence G.; WO2011/60000; (2011); A1;,
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Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.215453-51-3,7-Bromo-1-chloroisoquinoline,as a common compound, the synthetic route is as follows.,215453-51-3

Part D. 7-Bromo-1-phenoxyisoquinoline A solution of 3.60 g (14.8 mmol) of 7-bromo-1-chloroisoquinoline and 1.5 g of solid KOH in 11.2 g of phenol was heated at 140 C. for 2 hr. The reaction was cooled to room temperature, then partitioned between 100 mL of CH2Cl2 and 100 mL of 3N NaOH. The organic layer was washed with another 2*100 mL of 3N NaOH, then with 100 mL of H2O, and dried over MgSO4. Filtration and concentration gave a yellow oil, which was subjected to flash column chromatography on silica gel 30% CH2Cl2 in hexanes, giving 3.42 g (77%) of the desired product as a light yellow solid.

The synthetic route of 215453-51-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Cor Therapeutics, Inc.; US6399627; (2002); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem