Category: isoquinoline

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 50 mL dichloromethane solution containing (S)-3-hydroxymethy-1,2,3,4-tetrahydroisoquinoline (4.53 g, 27.75 mmol) was added di-tert-butyl dicarbonate (5.45 g, 25.0 mmol, 0.9 eq) and the reaction mixture was stirred for 2 hours until no gas bubbling was observed. The reaction mixture was washed with 0.5 N HCl (50 mL) followed by brine (50 mL) to remove the residual starting material. After drying wth MgSO4 and filtration , dichloromethane mixture was evaporated to yield crude (S)-N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline. The crude N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline was redissolved in 100 mL tetrahydrofuran. NaH (60%, 1.22 g) was added portion by portion to the solution at 0C and after 30 min stirring at room temperature, MeNCS (2.23 g) was added and the mixture was stirred for 2 h at rt. Brine (50 mL) was added to the mixture to quench the reaction and after evaporation of volatile in vacuo, it was extracted with dichloromethane (50mLx 2) and combined layer was dried (MgSO4), filtered, evaporated. The resulting material was chromatographed with hexane-EtOAc (4:1) mixture over SiO2 to provide 7.07 g-(81.8 %) of (S)-N-tert-butyloxycarbonyl-3-(N-Methyl-thiocarbamoyloxymethyl)-1,2,3,4-tetrahydroisoquinoline. This material was dissolved in THF(30 mL) and 10 mL conc. HCl was added to the solution. One hour later, 5 mL of conc, HCl was added and stirred another 1 h until the reaction is finished. The reaction mixture was diluted with 30 mL of water and volatile were evaporated. During the evaporation, desired product was precipitated as white solid. The solid was filtered and dried to yield the product as the hydrochloride salt (4.8 g). 1H-NMR (200 MHz, DMSO-d6) delta: 10.5-9.7 (m, 2H), 9.30 (s, 1H), 7.23 (s, 4H), 4.90 (m, 2H), 4.38 (s, 2H), 3.15-3.00 (m, 2H), 2.95 (d, 2H), 2.80 (1H)

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; SK Corporation; EP1149079; (2004); B1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.891785-28-7,6-Bromoisoquinolin-3-amine,as a common compound, the synthetic route is as follows.

891785-28-7, Step 1 To a stirred suspension of 6-bromoisoquinolin-3-amine (XX)(1.0 g, 4.48 mmol)in DMF (15 mL)at 0 C. was added 1-chloropyrrolidine-2,5-dione (XXI)(598.6 mg, 4.48 mmol)portionwise. The mixture was stirred at 0 C. for 6 h. The reaction mixture was added to water (150 mL), stirred for 1 h and the resulting solids were collected by filtration and air dried overnight to obtain 6-bromo-4-chloro-isoquinolin-3-amine (XXII)(922 mg, 3.58 mmol, 79.9% yield)as a beige solid which was used for next step without purification. 1H NMR (499 MHz, DMSO-d6)delta ppm 6.55 (2H, s), 7.40 (1H, dd, J=8.64, 1.78 Hz), 7.88 (1H, d, J=8.51 Hz), 7.90 (1H, d, J=1.10 Hz), 8.86 (1H, s); ESIMS found for C9H6BrClN2m/z 256.9 (79BrM+H).

The synthetic route of 891785-28-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Eastman, Brian Walter; Cao, Jianguo; Bollu, Venkataiah; Mittapalli, Gopi Kumar; Chiruta, Chandramouli; (218 pag.)US2017/313682; (2017); A1;,
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Isoquinoline | C9H7N – PubChem

190777-77-6, 5-Bromoisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a solution of bromomethyl derivative 9 or 12 and 18-crown-6 (1-2 mol%) in dry toluene (10 mL) was added K2CO3 (1.1 equiv) and KI (0.1 equiv) with stirring at r.t. for 10 min. The solution of isoquinolin-1(2H)-one 8a or 8b (1.2 equiv) in dry toluene (10 mL) was added slowly to the mixture. The mixture was then heated at reflux under argon for 24 h. After cooling, the mixture was filtered through a columnof Celite 545. The filtrate was concentrated under reduced pressure and the crude product was purified by flash column chromatography (silica gel, cyclohexane-EtOAc) to provide the expected products in good yields. 5-Bromo-2-[(2-chloroquinolin-3-yl)methyl]isoquinolin-1(2H)-one (13b). Following the general procedure using 8b (100 mg, 0.44 mmol), 18-crown-6 (2 mol%), K2CO3 (69 mg, 0.48 mmol), KI (7 mg, 0.44 mmol), and 3-(bromomethyl)-2-chloroquinoline (12, 343.5 mg, 0.53 mmol). The resulting crude mixture was purified by flash chromatography (cyclohexane-EtOAc, 9:1 to 1:1) to give a pale yellow solid; yield: 130 mg (74%); mp 209 C; Rf = 0.58 (cyclohexane-EtOAc, 3:2). 1H NMR (300 MHz, CDCl3, 25 C): delta = 5.41 (s, 2 H, CH2N), 6.88 (d, J =7.50 Hz, 1 H, CH), 7.33 (d, J = 6.90 Hz, 2 H, 2 CHarom), 7.51 (dd, J = 7.20, 7.50 Hz, 1 H, CHarom), 7.70 (d, J = 6.0 Hz, 2 H, 2 CHarom), 7.86 (s, 1 H, CHarom), 7.90 (d, J = 7.50 Hz, 1 H, CH), 8.01 (d, J = 9.0 Hz, 1 H, CHarom), 8.39 (d, J = 6.90 Hz, 1 H, CHarom). 13C NMR (75 MHz, CDCl3, 25 C): delta = 50.1 (CH2N), 105.5 (CHarom), 120.8 (Cq), 127.1 (Cq), 127.2 (Cq), 127.4 (CHarom), 127.5 (CHarom), 127.7 (CHarom), 128.2 (CHarom), 130.8 (CHarom), 132.9 (CHarom), 136.4 (CHarom), 137.2 (CHarom), 138.2 (CHarom), 142.2 (Cq), 147.1 (Cq), 147.8 (Cq), 149.4 (Cq), 161.6 (C=O). HRMS (ESI+): m/z found for C19H12BrClN2O (calcd): 398.9896 ([MH+], 398.9901), 400.0054 ([MH +1]+, 399.9901), 400.9880 ([MH + 2]+, 400.9901), 402.0011 ([MH + 3]+, 401.9901), 422.9704 ([M + 2 + Na]+, 422.9719)., 190777-77-6

The synthetic route of 190777-77-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; El Blidi, Lahssen; Namoune, Aurelie; Bridoux, Alexandre; Nimbarte, Vijaykumar D.; Lawson, Ata Martin; Comesse, Sebastien; Daich, Adam; Synthesis; vol. 47; 22; (2015); p. 3583 – 3592;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-04-8,5-Bromoisoquinoline,as a common compound, the synthetic route is as follows.

Example 57B 5-bromo-8-nitroisoquinoline The diethyl ether solution from Example 57A was treated with potassium nitrate (10.1 g, 100 mmol). After stirring for one hour, The mixture was poured onto ice and neutralized with concentrated ammonium hydroxide (~300 ml). The crude product was collected by filtration, dried, and recrystalization from methanol to provide the title compound (8.83 g)., 34784-04-8

As the paragraph descriping shows that 34784-04-8 is playing an increasingly important role.

Reference£º
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2004/157849; (2004); 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.622867-52-1,tert-Butyl 6-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate,as a common compound, the synthetic route is as follows.,622867-52-1

Intermediate 3 (185 mg, 0.264 mmol) and 1A (139 mg, 0.529 mmol) were dissolved in toluene (0.6 mL). Tris (n-butyl)phosphine (0.099 mL, 0.40 mmol) was added followed by TMAD (68.3 mg, 0.397 mmol), and the reaction mixture was stirred at rt overnight. The reaction mixture was filtered, and the filtrate was concentrated. The crude was purified by silica gel chromatography to yield 1B as a yellow solid (170 mg, 68.0 %). MS (ESI) m/z 945.1 (M+H).

The synthetic route of 622867-52-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne M.; HU, Carol Hui; VALENTE, Meriah Neissel; SHAW, Scott A.; VOKITS, Benjamin P.; HALPERN, Oz Scott; (137 pag.)WO2017/160632; (2017); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

18881-17-9, (S)-(1,2,3,4-Tetrahydroisoquinolin-3-yl)methanol is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,18881-17-9

To an ice cooled solution of 5-bromo-2-(3-(ethoxycarbonyl)-5-methyl-lH-pyrazol-l-yl)benzoic acid (45.0 g, 127.8 mmol) in DCM (450 mL) were added (5)-(l ,2,3,4-tetrahydroisoquinolin-3-yl)methanol (20.8 g, 102.27 mmol), HATU (72.7 g, 191.2 mmol), DIPEA (55.7 mL, 319.6 mmol) followed by stirring at RT for 12h. The reaction mixture was diluted with DCM (750 mL), washed with water (500 mL), brine (100 mL), dried over sodium sulphate and concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford the the title compound as a liquid 50 g (79%). Rf = 0.44 (55 % EtOAc in hexane); NMR (400 MHz, DMSO-d6): delta 8.00 – 7.40 (m, 3H), 7.30 – 7.00 (m, 4H), 6.80 – 6.40 (m, 1H), 5.10 – 3.80 (m, 7H), 3.50 – 2.40 (m, 3H), 2.40 – 2.10 (m, 3H), 1.30 – 1.00 (m, 3H); ES-MS: m/z 498.2 (M+H).

As the paragraph descriping shows that 18881-17-9 is playing an increasingly important role.

Reference£º
Patent; NOVARTIS AG; VISSER, Michael Scott; YUSUFF, Naeem; WO2013/96055; (2013); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

105627-79-0, Isoquinoline-5-sulfonyl chloride hydrochloride is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 1 52.8 g of 5-isoquinolinesulfonyl chloride hydrochloride was dissolved in 200 ml of water and extracted with 300 ml of dichloromethane. The resultant aqueous layer was taken out and adjusted to pH 5 with a saturated aqueous sodium hydrogencarbonate solution, and subjected to extraction with 200 ml dichloromethane. Then, the dichloromethane layers were mixed together and added dropwise to a dichloromethane solution (300 ml) containing 24.4 g of ethanolamine over 30 minutes while cooling with ice. The precipitated crystal was subjected to filtration, washed successively with 300 ml of water and 200 ml of ethyl acetate, and dried under reduced pressure at 40 C, to thereby obtain 40.0 g of N-(2-hydroxyethyl)-5-isoquinolinesulfonamide (yield: 79 %)., 105627-79-0

The synthetic route of 105627-79-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Asahi Kasei Kogyo Kabushiki Kaisha; EP471841; (1992); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

63927-23-1, 5-Bromo-8-nitroisoquinoline is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

63927-23-1, Iodomethane (506 mmol) was added to a solution of 5-bromo-8-nitroisoquinoline (101 mmol) in N,N-dimethylformamide (200 mL) and the reaction mixture was maintained for 16 h at 40 C. The precipitated solids were collected by filtration, washed with ether (2*250 mL), and dried to provide 5-bromo-8-nitro-N-methylisoquinolinium iodide in 83% yield as a red solid.

63927-23-1 5-Bromo-8-nitroisoquinoline 816983, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; Memory Pharmaceuticals Corporation; US2010/22581; (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.34551-41-2,5-Bromo-1-chloroisoquinoline,as a common compound, the synthetic route is as follows.

Step 3: Into a 500-mL round-bottom flask purged and maintained with an inertatmosphere of nitrogen, was placed a mixture of 5-bromo-1-chloroisoquinoline (17.5 g, 72.16mmol, 1.00 equiv), AcNH2 (85.8 g, 1.45 mol, 20.15 equiv) and potassium carbonate (49.0 g,354.53 mmol, 4.91 equiv). The mixture was stirred for 3 h at 180 C then it was cooled to RT and poured into 2000 mL of water with stirring. The solids were collected by filtration toprovide 12.0 g (75%) of 5-bromoisoquinolin-1-amine as a brown solid., 34551-41-2

The synthetic route of 34551-41-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLOBAL BLOOD THERAPEUTICS, INC.; LI, Zhe; ZANCANELLA, Manuel; YU, Chul; SETTI, Lina; SHAM, Hing; XU, Qing; YEE, Calvin; YU, Ming; (402 pag.)WO2016/201052; (2016); A1;,
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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 (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