Heterocyclic Building Blocks-Isoquinoline

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.106778-42-1,Isoquinoline-6-carbonitrile,as a common compound, the synthetic route is as follows.

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 (431mg, 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

The synthetic route of 106778-42-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Eisai Co., Ltd.; EP1669348; (2006); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

891785-30-1, 6-Bromo-3-fluoroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,891785-30-1

[00345] 3-Fluoroisoquinolin-6-ylboronic acid: A solution of 6-bromo-3- fluoroisoquinoline (9.10 g, 40.3 mmol) and triethylborate (1 1.8 g, 80.5 mmol) in THF (100 mL) was cooled to -78C. Butyllithium (1.6 M in hexanes 50.3 mL, 80.5 mmol) was added dropwise over 45 minutes. Over the course of the addition, the solution changed color from colorless to a light tan. The solution was stirred at -78C for 3 hours. The mixture was quenched with HCl (5 N, 120 mL) while in the cold bath at -78C, diluted with water (100 mL), and then extracted with EtOAc (3 x 200 mL). The combined organic layers were dried over Na2SO4, filtered and evaporated. The solid residue was triturated with DCM (200 mL), and the solid was recovered by filtration to provide the title compound (6.0 g, 78 %). LCMS (API-ES) m/z: 192 (M+H*).

891785-30-1 6-Bromo-3-fluoroisoquinoline 58488294, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; AMGEN INC.; WO2009/11880; (2009); A2;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

58142-99-7,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.58142-99-7,5-Iodoisoquinoline,as a common compound, the synthetic route is as follows.

Dissolve (trans)-4-methylhexahydropyrrole[3,4-b][1,4]oxazine (333 mg, 2.3 mmol) in toluene (20 mL)Add triethylamine (2 mL), 5-iodoisoquinoline (718 mg, 2.8 mmol), XPhos (110 mg, 0.23 mmol), cesium carbonate (2.25 g, 6.9 mmol) and palladium acetate (52 mg) successively. , 0.23 mmol), heated to 90C under nitrogen atmosphere overnight. The mixture was filtered off with suction and the filtrate was concentrated and purified by column chromatography to give the title compound (600 mg).

The synthetic route of 58142-99-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Liu Gang; Wu Yongyong; Yu Hua; Wang Kunjian; Li Xiaoyong; Sun Ling; Wang Runjiang; Chen Qiangqiang; Yang Long; Song Hongmei; Zeng Hong; Zhang Hong; Ye Qijun; Wang Lichun; Wang Jingyi; (98 pag.)CN107540659; (2018); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-02-6,3-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

Example 5 – Preparation of Precursor 282 Precursor 271 Precursor 282 To a dry, nitrogen-flushed flask was charged with Precursor 271 (0.20 g, 0.37 mmol), potassium teri-butoxide (0.05 g, 0.44 mmol), Pd(dba)2 (0.03 g, 0.03 mmol), DPE-phos (0.04 g, 0.07 mmol), 3-bromoisoquinoline (0.08 g, 0.86 mmol), and anhydrous toluene. The mixture was refluxed for 24 h. After cooling to room temperature, ethyl acetate was added, and the mixture was stirred for five minutes. The crude mixture was extracted with ethyl acetate and purified by chromatography on silica gel with mixture of hexane and ethyl acetate (v/v = 10: 1). 0.17 g of yellow solid was obtained. Yield: 69 %. H NMR (CDC13, 300 MHz): delta 9.03 (s, 1H), 8.00 (s, 1H), 7.83-7.96 (m, 4H), 7.69 (s, 1H), 7.53-7.45 (m, 6H), 7.39-7.30 (m, 5H), 7.25-7.23 (m, 2H), 7.15-7.02 (m, 4H), 3.85 (s, 3H), 1.37 (s, 18H)., 34784-02-6

The synthetic route of 34784-02-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; THE UNIVERSITY OF HONG KONG; CHE, ChiMing; KUI, ChiFai; KWOK, Chi Chung; WO2013/152727; (2013); 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 meta-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 in vacuo to afford Cap-138, step b (2.15 g, 83%) as a pale, yellow solid which was sufficiently pure to carry forward directly. 1H NMR (CDCl3, 400 MHz) delta 8.73 (d, J=1.5 Hz, 1H), 8.11 (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.-D1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C10H10NO2: 176.07; found: 176.0.

90806-58-9 5-Methoxyisoquinoline 13754283, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Bristol-Myers Squibb Company; US2010/249190; (2010); 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.34784-02-6,3-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

Typical procedure for the palladium-catalyzed domino reaction of the 1,6-diynes with bromo(iso)quinoline: diyne 1a-p (1.0 equiv), 3-bromoquinoline (1.2 equiv), Pd(OAc)2 (2 mol %), and PPh3 (4 mol %) were added to the degassed solution of (n-Bu)3N (1.2 equiv) in DMF (5 mL) and the mixture was stirred at room temperature for 40 min then heated at 125-130 C for 24 h. The reaction mixture was cooled, quenched with water, and extracted with EtOAc (3¡Á5 mL). The combined organic layers were washed with hydrochloric acid (5%), aqueous sodium carbonate (5%), and saturated aqueous sodium chloride solution. After separation, the organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (6:1 petroleum ether/EtOAc) to give the corresponding product 3.

34784-02-6, The synthetic route of 34784-02-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hu, Yimin; Zhu, Tao; Mu, Xiaolong; Zhao, Quansheng; Yu, Tao; Wen, Lei; Zhang, Yulong; Wu, Min; Zhang, Hao; Tetrahedron; vol. 68; 1; (2012); p. 311 – 318;,
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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13130-79-5,1-Bromoisoquinolin-3-amine,as a common compound, the synthetic route is as follows.

To 1-(4-methoxyphenyl)cyclopropanecarboxylic acid (4.07 g, 21.17 mmol), thionyl chloride (4.64 mL, 63.52 mmol) and DMF (64 muL) were stirred at 50 C. for 3 hours, after which additional thionyl chloride (4 mL) and DMF (60 muL) were added and the mixture was stirred at 50 C. for 1 additional hour. The excess thionyl chloride was evaporated under reduced pressure. The resulting acid chloride was dissolved in anhydrous DCM (20 mL) and was slowly added to a cooled suspension of (0 C.) of 1-bromoisoquinolin-3-amine in DCM (50 mL) and Et3N (14.05 mL, 100.8 mmol). The reaction mixture was stirred at room temperature for 18 hours. The resulting mixture was diluted with DCM and washed with water (1¡Á30 mL), 1 N NaOH (2¡Á30 mL), 1 N HCl (1¡Á30 mL), saturated aqueous NaHCO3 (1¡Á30 mL) and brine (1¡Á30 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-50% ethyl acetate in hexane) to yield N-(1-bromoisoquinolin-3-yl)-1-(4-methoxyphenyl)cyclopropanecarboxamide (6.0 g, 75%) as a yellow solid. ESI-MS m/z calc. 396.05, found 397.3 (M+1)+. Retention time 2.24 minutes. 1H NMR (400.0 MHz, CDCl3) d 8.55 (s, 1H), 8.15 (d, J=8.5 Hz, 1H), 7.89 (s, 1H), 7.78 (d, J=8.2 Hz, 1H), 7.69-7.65 (m, 1H), 7.56-7.52 (m, 1H), 7.46-7.42 (m, 2H), 7.01-6.98 (m, 2H), 3.90 (s, 3H), 1.75 (dd, J=3.7, 6.8 Hz, 2H) and 1.21 (dd, J=3.7, 6.9 Hz, 2H) ppm.

13130-79-5, As the paragraph descriping shows that 13130-79-5 is playing an increasingly important role.

Reference£º
Patent; HADIDA RUAH, SARA S.; Miller, Mark; Zhou, Jinglan; Bear, Brian; Grootenhuis, Peter; US2009/143381; (2009); A1;,
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27810-64-6, Isoquinoline-5-carboxylic acid is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

192A. N-(l-Methylpiperidin-4-yl)isoquinoline-5-carboxamide: To isoquinoline- 5-carboxylic acid (0.22 g, 1.270 mmol) and l-methylpiperidin-4-amine (0.145 g, 1.270 mmol) in EtOAc (3 mL)/DMF(l mL) was added TEA (0.48 mL, 3.464 mmol) and a 50% EtOAc solution of T3P (0.306 mL, 1.082 mmol). After 24h, the reaction was partitioned with water (15 mL) and ethyl acetate (50 mL). The organic layer was washed with brine (10 mL) and dried (MgS04). MS (ESI) m/z: 270.1 (M+H)+., 27810-64-6

As the paragraph descriping shows that 27810-64-6 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.P.; CLARK, Charles G.; SMITH, II, Leon M.; ORWAT, Michael J.; JEON, Yoon; CORTE, James R.; WO2014/160668; (2014); 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.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

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7651-81-2,Isoquinolin-3(2H)-one,as a common compound, the synthetic route is as follows.

tert-butyl 3-(hydroxymethyl)-2-azabicyclo[3.1.1]heptane-2-carboxylate (p14, 100 mg, 0.44 mmol) was dissolved in THF (7 mL). PP (174 mg, 0.66 mmol) was added, followed by 3-hydroxyisoquinoline (96 mg, 0.66 mmol). The mixture was stirred at RT for 15′, then cooled to 0 C. Di-tert-butyl azodicarboxylate (152 mg, 0.66 mmol) was added portionwise and, after 10′, the ice bath was removed, allowing the mixture to stir at RT for 1 .5h. The mixture was concentrated under vacuum to obtain a crude that was combined with crude from a similar preparation. Combined crude material was purified by FC on silica gel (eluent from Cy to EtOAc 20%) to afford tert-butyl 3-[(isoquinolin-3- yloxy)methyl]-2-azabicyclo[3.1.1 ]heptane-2-carboxylate (p16, 72 mg, 30% recovery on combined batches) as colourless oil. MS (mlz): 355.3 [MH]+., 7651-81-2

Big data shows that 7651-81-2 is playing an increasingly important role.

Reference£º
Patent; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem