Day: March 7, 2022

104704-40-7, 4-Bromo-1-methylisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example No. 130: Preparation of Compound No. 164[0418] A solution of 2, 8-dimethyl-2, 3, 4, 5-tetrahydro- lH-pyrido[4,3-b]indole (310 mg, 1.55 mmol), K3P04 (0.985 g, 4.65 mmol), Cul (29.4 mg, 0.15 mmol), L-proline (35.6 mg, 0.31 mmol) and 4-bromo-l-methylisoquinoline (0.520 g, 2.35 mmol) in dry DMF (3 mL) was stirred at RT for 10 min and then at 150 C for 16h. Water (50 mL) was added to the reaction mixture and then extracted with EtOAc (150 mL). The organic layer was washed with water (6×30 mL), dried over anhydrous sodium sulfate and evaporated to afford crude material, which was purified by reverse phase HPLC to yield 2,8-dimethyl-5-(l-methylisoquinolin-4-yl)-2,3,4,5-tetrahydro- lH-pyrido[4,3-b]indole as the TFA salt. 1H NMR (CD3OD, TFA salt) delta (ppm): 8.6-8.74 (m,2H), 8.0 (m, 2H), 7.41 (s, IH), 7.38 (bs, IH), 7.0 (d, IH), 6.8 (bs, IH), 4.8 (bs, IH), 4.5 (bs, IH), 3.8 (bs, IH), 3.6 (bs, IH), 3.3 (s, 3H), 3.18 (s, 3H), 3.0 (bs, IH), 2.82 (bs, IH), 2.41 (s, 3H)., 104704-40-7

As the paragraph descriping shows that 104704-40-7 is playing an increasingly important role.

Reference：
Patent; MEDIVATION TECHNOLOGIES, INC.; PROTTER, Andrew, Asher; CHAKRAVARTY, Sarvajit; WO2012/112962; (2012); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1242157-15-8,6-Bromo-8-fluoro-3,4-dihydroisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

1242157-15-8, To a stirred solution of CD3OD (CAS 811-98-3; 3.1 mL, 76.2 mmol, 6 eq.) in THF (31 mL) at 0 C is added portionwise NaH (60% dipersion in mineral oil, 366 mg, 15.24 mmol, 1.2 eq.). The reaction mixture is stirred at 0 C for 20 min and 6-bromo-8-fluoro-3,4-dihydro-2H-isoquinolin-l-one (CAS 1242157-15-8, 3.1 g, 12.7 mmol, 1 eq.) is added in one portion. The reaction is stirred at RT for 1.5 h and NaH (60% dipersion in mineral oil, 60 mg, 2.5 mmol, 0.2 eq.) is added. The reaction mixture is stirred at RT for 18 h. The reaction mixture is quenched with a sat. NH4CI solution. THF is evaporated and water (31 mL) is added to the suspension.The suspension is stirred at RT for 1 h and then filtered. The solid is rinsed with water and dried under vacuum to afford the expected product.

The synthetic route of 1242157-15-8 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; GALAPAGOS NV; DESROY, Nicolas; JONCOUR, Agnes, Marie; PEIXOTO, Christophe; TEMAL-LAIB, Taoues; TIRERA, Amynata; BUCHER, Denis; AMANTINI, David; DE VOS, Steve, Irma, Joel; BRYS, Reginald, Christophe, Xavier; (396 pag.)WO2019/238424; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

258515-65-0, tert-Butyl 7-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

7b 7-lodo-3,4-dihydro-1 /-/-isoquinoline-2-carboxylic acid te/f-butyl ester To 11.0 g (35.2 mmol) 7-bromo-3,4-dihydro-1 /-/-isoquinoline-2-carboxylic acid te/f-butyl ester (preparation 7a) in 35 mL 1 ,4-1 ,4-dioxanee is added 692 mg (3.56 mmol) copper(l)-iodide under argon. After flushing with argon, 0.75 mL (7.05 mmol) lambda/,lambda/-dimethylethylen-diamine and 10.6 g (70.5 mmol) sodium-iodide is added at RT. The reaction mixture is stirred 14 h at 1 100C, cooled to RT and diluted with 5% aqueous ammonia-solution. The aqueous phase is extracted with EtOAc and the combined organic phase is washed with water, dried over MgSO4. After filtration and evaporation of the solvent, the residue is purified via chromatography (silica gel; Cyclohexane/EtOAc 85/15). Yield: 10.8 g (purity 75% (contains compound 7a), 78% of theory) ESI Mass spectrum: [M+H]+ = 360 Rf-value: 0.6 (silica gel, mixture F)., 258515-65-0

The synthetic route of 258515-65-0 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BOEHRINGER INGELHEIM PHARMA GMBH & CO. KG; WO2008/22979; (2008); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

724422-42-8, 6-Bromo-2-methyl-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,724422-42-8

To a solution of compound 64.3 (0.25 g, 1.04 mmol, 1.0 eq) in toluene (1.0 mL) was added benzophenonimine (0.21 g, 1.14 mmol, 1.1 eq) and NaOBut (0.15 g, 1.56 mmol, 1.5 eq). The mixture was degassed for 10 minutes using argon, then Pd2(dba)3 (0.009 g, 0.01 mmol, 0.01 eq) and BINAP (0.029 g, 0.052 mmol, 0.05 eq) were added. The reaction was then heated at 100 C. for 8 hours. After completion, reaction mixture was poured into water and product was extracted with EtOAc. Organic layers were combined, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to obtain crude material. The crude was purified by column chromatography to provide 64.4 (0.04 g, 21.8%). MS(ES): m/z 176.22 [M+H]+.

As the paragraph descriping shows that 724422-42-8 is playing an increasingly important role.

Reference：
Patent; Nimbus Lakshmi, Inc.; Dahlgren, Markus; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Kennedy-Smith, Joshua Jahmil; Masse, Craig E.; Romero, Donna L.; Shelley, Mee; Wester, Ronald T.; (131 pag.)US2016/251376; (2016); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

724422-42-8, 6-Bromo-2-methyl-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,724422-42-8

A mixture of 6-bromo-2-methyl-3,4-dihydroisoquinolin-1-one (1 g, 0.00418 mol), bis(pinacolato)diboron (1.59 g, 0.00627 mol) and potassium acetate (1.2 g, 0.0125 mol) were dissolved in DMF (15 mL) and the mixture was degassed with nitrogen for 15 min. Then, a catalytic amount of PdCl2(dppf).CH2Cl2 (0.17 g, 0.0002 mol) was added and purging with nitrogen continued for 5 min. Then the mixture was heated at 80 C. for 2 h. The reaction was monitored by TLC and 1HNMR. After completion of reaction, the mixture was diluted with water (50 mL) and extracted with EtOAc (2*100 mL). The combined organic layer was washed with water (2*50 mL) and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain a crude product, which was purified by chromatography using eluent 40% EtOAc in hexane to obtain 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinolin-1-one (890 mg) as a light yellow oil.

As the paragraph descriping shows that 724422-42-8 is playing an increasingly important role.

Reference：
Patent; Medivation Technologies LLC; Pujala, Brahmam; Jangir, Ramniwas; Guguloth, Rambabu; Shinde, Bharat Uttam; Rai, Roopa; Pham, Son Minh; Bernales, Sebastian; Lindquist, Jeffrey; Guha, Mausumee; Kallem, Satyanarayana; Bhatt, Bhawana; Bhagwat, Vikas Ramdas; (162 pag.)US2018/51013; (2018); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem