Heterocyclic Building Blocks-Isoquinoline

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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3336-60-5, 1-Chloro-4-methoxyisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 2: Preparation of 1-Fluoro-4-methoxyisoquinoline To a solution of 1-chloro-4-methoxyisoquinolin (2.5 g, 12.91 mmol) in DMSO was added cesium fluoride (4.01 g, 25.82 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 145¡ã C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (700 mg, 62percent) as a white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.10 (m, 1H), 8.08 (m, 1H), 7.78-7.75 (m, 1H), 7.69-7.65 (m, 1H), 7.49 (m, 1H), 4.04 (s, 3H); 19F NMR: delta ppm -78.66 (1F); MS:MS m/z 178.1 (M++1)., 3336-60-5

As the paragraph descriping shows that 3336-60-5 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; Nagalakshmi, Pulicharla; Sarkunam, Kandhasamy; Renduchintala, Kishore V.; Scola, Paul Michael; (62 pag.)US2015/376233; (2015); A1;,
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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;,
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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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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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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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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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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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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;,
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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

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;,
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