Downstream synthetic route of 226942-29-6

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 6-bromo tetrahydroisoquinoline (300 mg, 1.42 mmol) in CH2Cl2 (8 mL) was cooled to 0 C, and i-Pr2NEt (243 mg, 1.88 mmol) and CbzCl (322 mg, 1.88 mmol) were added. The reaction was stirred at room temperature for 16 h. The reaction was diluted with CH2Cl2 (10 mL) and poured into water (20 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3 x 20 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The crude mixture was purified via flash column chromatography eluting with EtOAc:hexanes (5:95) to give 400 mg (81%) of 9 as a colorless oil: 1H NMR (400 MHz) delta 7.41 – 7.27 (comp, 7 H), 6.97 (d, J = 10.3 Hz, 1 H), 5.18 (s, 2 H), 4.59 (s, 2 H), 3.70 (br s, 2 H), 2.82 (br s, 2 H); HRMS (ESI) m/z C17H16BrNO2 (M+Na)+ calcd for 368.0257 and 370.0238; found 368.0257 and 370.0238.

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

Reference£º
Article; Linkens, Kathryn; Schmidt, Hayden R.; Sahn, James J.; Kruse, Andrew C.; Martin, Stephen F.; European Journal of Medicinal Chemistry; vol. 151; (2018); p. 557 – 567;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Simple exploration of 226942-29-6

226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various.

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

6-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinolineTo a solution of 6-bromo-1 ,2,3,4-tetrahydroisoquinoline (1 g, 4.72 mmol) in formic acid (10 mL, 261 mmol) was added formaldehyde (37%) (2 mL, 72.6 mmol). The reaction was stirred at 150 C for 15 min in a microwave reactor. T he reaction mixture was concentrated under vaccum, cooled to 0 C, quenched with saturated NaHC03solution, extracted with EtOAc (2X), The organic layer washed with brine, dried under anhydrous Na2S04and filtered. The filtrate was reduced under pressure to afford 6-bromo-2-methyl- 1 ,2,3,4-tetrahydroisoquinoline (900 mg, 3.85 mmol, 82 % yield). LC-MS m/z 226 (M+H)+, 1.29 min (ret. time). The crude compound was used for next step without further purification.

226942-29-6 6-Bromo-1,2,3,4-tetrahydroisoquinoline 15885183, atetrahydroisoquinoline compound, is more and more widely used in various.

Reference£º
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; ASTEX THERAPEUTICS LIMITED; BOEHM, Jeffrey Charles; DAVIES, Thomas Glanmor; WOOLFORD, Alison Jo-anne; GRIFFITHS-JONES, Charlotte Mary; WILLEMS, Hendrika Maria Gerarda; NORTON, David; SAXTY, Gordon; HEIGHTMAN, Thomas Daniel; LI, Tindy; KERNS, Jeffrey K.; DAVIS, Roderick S.; YAN, Hongxing; WO2015/92713; (2015); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Downstream synthetic route of 226942-29-6

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of Boc-L-proline (Int-5a, 406 mg, 1.88 mmol) in 10 mL of DMF was added amine Int-6a (400 mg, 1.88 mmol), EDCI (450 mg, 2.35 mmol), HOBT (317 mg, 2.35 mmol), and Hunig’s base (0.65 mL, 3.76 mmol). The resulting reaction was heated at 85 0C and allowed to stir at this temperature for 16 hours. The reaction mixture was cooled to room temperature and was then partitioned between EtOAc and water. The organic phase was separated and the aqueous phase was further extracted with EtOAc. The combined organic phases were dried (MgSO4) and concentrated in vacuo to provide a crude residue which was purified using (ISCO) flash column chromatography (EtO Ac/Hex, 0 to 50% EtOAc eluent ) to provide compound Int-6b (680 mg, 88%).

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

Reference£º
Patent; SCHERING CORPORATION; ROSENBLUM, Stuart, B.; CHEN, Kevin, X.; KOZLOWSKI, Joseph, A.; NJOROGE, F., George; COBURN, Craig, A.; WO2010/132538; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

New learning discoveries about 226942-29-6

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of the acid structural unit S27 (1.5 g) in dichloromethane (5 ml/mmol) there was added at 0 C. diisopropylethylamine (2.5 eq.), followed by N-hydroxybenzotriazole (HOBt) (1 eq.) and N-ethyl-N’-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI) (1.5 eq.). The resulting reaction mixture was stirred for 15 min. at 23 C. It was then cooled to 0 C., and 6-bromo-1,2,3,4-tetrahydroisoquinoline (1.2 eq., dissolved in dichloromethane) was added dropwise. The reaction mixture was stirred for 16 h at 25 C. until the reaction was complete. The mixture was diluted with dichloromethane (100 ml) and extracted with saturated ammonium chloride solution, saturated sodium chloride solution, saturated sodium hydrogen carbonate solution and again with saturated sodium chloride solution. The organic phase was dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (5% ethyl acetate in dichloromethane). Yield: 80%

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Gruenenthal GmbH; US2008/153843; (2008); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

New learning discoveries about 226942-29-6

As the paragraph descriping shows that 226942-29-6 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.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

Step 2 Sodium bicarbonate (1.21 kg) and Boc2O (2.62 kg) were added to a solution of 6-bromo-1,2,3,4tetrahydroisoquinoline (2.55 kg, 12.02 mol, 1.00 equivalent) in ethyl acetate (12.5 L) and water (12.5 L) at 20 C., and the reaction solution was stirred at 20 C. for 12 hours. After the reaction was completed, the reaction mixture was allowed to stand for layering, and the aqueous phase was extracted again with ethyl acetate (10 L*2). The organic phases were combined and washed once with water (10 L), dried over anhydrous sodium sulfate, filtered and concentrated to give N-tert-butoxycarbonyl-6bromo-1,2,3,4-tetrahydroisoquinoline (3.5 kg, 11.21 mol, yield of 91.4%, purity of 98%) as a yellow oil. m/z 256, 258 (1:1) [M+H-56]+; 1H NMR (400 MHz, CDCl3) delta=7.29 (m, 2H), 6.98 (d, 1H), 4.51 (s, 2H), 3.63 (t, 2H), 2.81 (t, 2H), 1.49 (s, 9H).

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

Reference£º
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; YAN, Xiaobing; HUANG, Wei; LI, Dan; DING, Charles Z.; LIU, Fei; ZHANG, Xiquan; (26 pag.)US2019/284146; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Brief introduction of 226942-29-6

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: 1007511 To a mixture of Compound 61F (250 mg, 0.5 mmol) and Cs2CO3 (326 mg, 1 mmol) in DMF (20 mL) was added Mel (142 mg, 1 mmol) and stirred at 60 C for 3 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 50% v/v) to afford Compound 63A. LC-MS (ESI) m/z: 518 [M+H]t

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Analyzing the synthesis route of 226942-29-6

The synthetic route of 226942-29-6 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.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

To a solution of Boc-L-proline (Int-15a, 406 mg, 1.88 mmol) in 10 mL of DMF was added amine Int-16a (400 mg, 1.88 mmol), EDCI (450 mg, 2.35 mmol), HOBT (317 mg, 2.35 mmol), and diisopropylethylamine (0.65 mL, 3.76 mmol). The resulting reaction was heated at 85 0C and allowed to stir at this temperature for 16 hours. The reaction mixture was cooled to room temperature and was then partitioned between EtOAc and water. The organic phase was separated and the aqueous phase was further extracted with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to provide a crude residue which was purified using (ISCO) flash column chromatography (EtO Ac/Hex, 0 to 50% EtOAc eluent ) to provide Compound Int-16b (680 mg, 88%).

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; SCHERING CORPORATION; ZENG, Qingbei; CHEN, Kevin, X.; ANILKUMAR, Gopinadhan, N.; ROSENBLUM, Stuart, B.; KOZLOWSKI, Joseph, A.; NJOROGE, F., George; WO2010/138791; (2010); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Analyzing the synthesis route of 226942-29-6

The synthetic route of 226942-29-6 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.226942-29-6,6-Bromo-1,2,3,4-tetrahydroisoquinoline,as a common compound, the synthetic route is as follows.

A mixture of 4-chloro-benzo[4,5]furo[3,2-d]pyrimidine (1.06 g, 5.19 mmol), 6-bromo-l,2,3,4- tetrahydroisoquinoline (1.0 g, 4.7 mmol), potassium carbonate (1.95 g, 14.1 mmol) and sodium iodide (0.71 g, 4.7 mmol) in dioxane (50 mL) was heated at 90 C for 6 hrs. The mixture was diluted with EtOAc and washed with water, brine, dried over Na2S04 and concentrated. The residue was purified by recrystallization with EtOAc to give 4-(6- bromo-3,4-dihydroisoquinolin-2(lH)-yl)benzofuro[3,2-d]pyrimidine (1.2 g, 3.16 mmol, 66.9 % yield). LCMS (M+H): 379.90, 381.90.

The synthetic route of 226942-29-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; DESKUS, Jeffrey; EASTMAN, Kyle J.; GILLIS, Eric P; FRENNESSON, David B; IWUAGWU, Christiana; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PEESE, Kevin M; SAULNIER, Mark G; SIVAPRAKASAM, Prasanna; (220 pag.)WO2018/127801; (2018); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem

Downstream synthetic route of 226942-29-6

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

226942-29-6, 6-Bromo-1,2,3,4-tetrahydroisoquinoline is a tetrahydroisoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirred solution of 6-bromo-1,2,3,4-tetrahydroisoquinoline (1000 mg, 4.7 mmol) and triethylamine (1.0 mL, 7.0 mmol) in DCM (20 mL) was added trimethyl acetyl chloride (0.64 mL, 5.2 mmol) at 0 C and the solution stirred at 25 C for 2 h. Water (60 mL) was added and extracted with DCM (30 mL x3), the combined organics were washed with brine and dried over Na2SO4. The solution was filtered and reduced in vacuo to afford 1-(6-bromo-3,4-dihydro-1H-isoquinolin-2-yl)-2,2-dimethylpropan-1-one (1390 mg, 4.7 mmol, 99% yield) as a light-yellow solid. UPLC-MS (ES+, Method F), 4.02 min, m/z 298.0 [M+H]+

As the paragraph descriping shows that 226942-29-6 is playing an increasingly important role.

Reference£º
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
Tetrahydroisoquinoline – Wikipedia
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem