Some tips on 3336-43-4

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3336-43-4,1-Chloroisoquinolin-4-ol,as a common compound, the synthetic route is as follows.

The mixture of 1-chloroisoquinolin4-ol (0.5 g, 2.8 mmol) and [6-({[tert- butyl (dimethyl) silyl] oxy} methyl) pyridin-2-yl] methyl methanesulfonate (0.9 g, 2.8 mmol) in anhydrous DMF (15 mL) was treated with potassium hydroxide (0.16 g, 2.8 mmol) at rt. After 12, the mixture was partitioned between saturated aqueous NaHC03 (10 mL) and EtOAc (20 mL). The phases were separated and the aqueous layer was extracted with EtOAc (3 x 20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was purified on silica gel (20: 1 hexane-ethyl acetate) to provide 4-{ [6-({ [tert-butyl (dimethyl) silyl] oxy} methyl) pyridin-2-yl] methoxy}-1-chloroisoquinoline as an orange oil : LRMS (ESI) m/z 416 (416 calcd for C22H27ClN202Si, M+H).

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

Reference£º
Patent; MERCK & CO., INC.; WO2005/41971; (2005); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Brief introduction of 3336-43-4

3336-43-4, 3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various fields.

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: Preparation of 1-chloro-4-ethoxyisoquinoline To a solution of 1-chloroisoquinolin-4-ol (1.0 g, 5.5 mmol) in acetonitrile (10 mL) was added K2CO3 (2.3 g, 16.7 mmol) followed by ethyl iodide (0.87 ml, 11.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined 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 1-chloro-4-ethoxyisoquinoline (0.7 g, 62%) as off-white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.26-8.24 (m, 2H), 7.79 (s, 1H), 7.76-7.26 (m, 2H), 4.29-4.24 (q, J=6.8 Hz, 2H), 1.58-1.54 (t, J=6.8 Hz, 3H); MS: MS m/z 207.7 (M++1).

3336-43-4, 3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various fields.

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;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

New learning discoveries about 3336-43-4

The synthetic route of 3336-43-4 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.3336-43-4,1-Chloroisoquinolin-4-ol,as a common compound, the synthetic route is as follows.

To a solution of 1-chloroisoquinolin-4-ol (1.0 g, 5.5 mmole) in acetonitrile (10 mL) was added K2CO3(2.3 g, 16.7 mmole) followed by ethyl iodide (0.87 mL, 11.0 mmole) at room temperature. The reaction mixture was stirred at room temperature for overnight. Solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated under reduced. The resulting residue was purified by silica gel chromatography to afford 1-chloro-4-ethoxyisoquinoline (700 mg, 62%) as an off-white solid.1H NMR (400 MHz, CD3OD): delta ppm 8.26-8.24 (m, 2H), 7.79 (s, 1H), 7.76-7.26 (m, 2H), 4.29-4.24 (q, J=6.8 Hz, 2H), 1.58-1.1.54 (t, J=6.8 Hz, 3H); MS: MS m/z 207.7 (M++1)., 3336-43-4

The synthetic route of 3336-43-4 has been constantly updated, and we look forward to future research findings.

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; (403 pag.)US9527885; (2016); B2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Some tips on 3336-43-4

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3336-43-4,1-Chloroisoquinolin-4-ol,as a common compound, the synthetic route is as follows.

Step 1: Preparation of 1-chloro-4-ethoxyisoquinoline To a solution of 1-chloroisoquinolin-4-ol (1.0 g, 5.5 mmol) in acetonitrile (10 mL) was added K2CO3 (2.3 g, 16.7 mmol) followed by ethyl iodide (0.87 ml, 11.0 mmol) at room temperature. The reaction mixture was stirred at room temperature for overnight. The solvent was evaporated under reduced pressure and the residue was diluted with water and extracted with ethyl acetate. The combined 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 1-chloro-4-ethoxyisoquinoline (0.7 g, 62%) as off-white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.26-8.24 (m, 2H), 7.79 (s, 1H), 7.76-7.26 (m, 2H), 4.29-4.24 (q, J=6.8 Hz, 2H), 1.58-1.54 (t, J=6.8 Hz, 3H); MS: MS m/z 207.7 (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; Rajamani, Ramkumar; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Meanwell, Nicholas A.; Scola, Paul Michael; US2013/142754; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Simple exploration of 3336-43-4

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

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: Preparation of 1-chloro-4-methoxyisoquinoline To a solution of 1-chloroisoquinolin-4-ol (5.0 g, 27.8 mmol) in acetonitrile (50 mL) was added TMS-diazomethane (12.73 g, 111.2 mmol) at 0 C. The reaction mixture was allowed to come to room temperature and stirred for 2 h. Solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-methoxyisoquinoline (2.5 g, 46.4%) as off-white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.29-8.17 (m, 2H), 7.97 (s, 1H), 7.91-7.82 (m, 2H), 4.05 (s, 3H); MS: MS m/z 194.7 (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;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Analyzing the synthesis route of 3336-43-4

3336-43-4, 3336-43-4 1-Chloroisoquinolin-4-ol 4281882, 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.3336-43-4,1-Chloroisoquinolin-4-ol,as a common compound, the synthetic route is as follows.

To a solution of 1-chloroisoquinolin-4-ol (5.0 g, 27.8 mmol) in acetonitrile (50 mL) was added TMS-diazomethane (12.73 g, 111.2 mmol) at 0¡ã C. The reaction mixture was allowed to come to room temperature and stirred for 2 h. Solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-methoxyisoquinoline (2.5 g, 46.4percent) as off-white solid.1H NMR (400 MHz, CD3OD): delta ppm 8.29-8.17 (m, 2H), 7.97 (s, 1H), 7.91-7.82 (m, 2H), 4.05 (s, 3H); MS: MS m/z 194.7 (M++1).

3336-43-4, 3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various fields.

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; (403 pag.)US9527885; (2016); B2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Brief introduction of 3336-43-4

3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various fields.

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: Preparation of 1-chloro-4-methoxyisoquinoline To a solution of 1-chloroisoquinolin-4-ol (5.0 g, 27.8 mmol) in acetonitrile (50 mL) was added TMS-diazomethane (12.73 g, 111.2 mmol) at 0 C. The reaction mixture was allowed to come to room temperature and stirred for 2 h. Solvent was evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get 1-chloro-4-methoxyisoquinoline (2.5 g, 46.4%) as off-white solid. 1H NMR (400 MHz, CD3OD): delta ppm 8.29-8.17 (m, 2H), 7.97 (s, 1H), 7.91-7.82 (m, 2H), 4.05 (s, 3H); MS: MS m/z 194.7 (M++1)., 3336-43-4

3336-43-4 1-Chloroisoquinolin-4-ol 4281882, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; Rajamani, Ramkumar; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Meanwell, Nicholas A.; Scola, Paul Michael; US2013/142754; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Simple exploration of 3336-43-4

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

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 1-chloroisoquinolin-4-ol (0.5 g, 2.78 mmol), 1-bromo-2-methoxyethane (0.318 mL, 3.34 mmol), and potassium carbonate (0.539 g, 3.90 mmol) were added to a solution of DMF (10 mL) and heated to 45 C. for 1 hr. Ater 45 min, the temp was raised to 55 C. for 45 min. One half of an equivalent of 1-bromo-2-methoxyethane (0.318 mL, 3.34 mmol) was then added and then stirred at 40 C. for overnight. The reaction was diluted with water and extracted with EtOAc. The organic layer was washed with brine, collected, dried over MgSO4, filtered and evaporated to give the crude product. Crude material purified via silica gel chromatography (10-60% EtOAc:Hex) to give the desired product 1-chloro-4-(2-methoxyethoxy)isoquinoline (368 mg, 1.548 mmol, 55.6% yield) as an orange solid. 1H NMR (400 MHz, CHLOROFORM-d) delta 8.33-8.24 (m, 2H), 7.83 (s, 1H), 7.81-7.68 (m, 2H), 4.40-4.32 (m, 2H), 3.95-3.84 (m, 2H), 3.52 (s, 3H). MS: MS m/z 238.15 (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;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Some tips on 3336-43-4

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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.3336-43-4,1-Chloroisoquinolin-4-ol,as a common compound, the synthetic route is as follows.

l-Chloro-4-hydroxyisoquinone (790 mg, 4.4 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde ( 1.077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 mu, 1.46 mmol) and then stirred at 80 C under LC-MS control for 24 h. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and the precipitates were collected by filtration, washed well with 50 % aqueous ethanol and dried under vacuum to yield the title compound (1.7 g, 3.6 mmol, 82 %).

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

Reference£º
Patent; DEUTSCHES KREBSFORSCHUNGSZENTRUM (DKFZ); RUPRECHTS-KARLS-UNIVERSITAeT HEIDELBERG; BOUTROS, Michael; MASKEY, Rajendra-Prasad; KOCH, Corinna; FUCHS, Florian; STEINBRINK, Sandra; GILBERT, Daniel; WO2012/62905; (2012); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

 

Simple exploration of 3336-43-4

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

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;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem