22246-12-4| Page 5 of 5 | Heterocyclic Building Blocks-Isoquinoline

Some tips on 22246-12-4

The synthetic route of 22246-12-4 has been constantly updated, and we look forward to future research findings.

22246-12-4, 6-Methoxy-3,4-dihydroisoquinolin-1(2H)-one is a isoquinoline compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Intermediate A6 2-(4-isobutylphenyl)-6-methoxy-3.4-dihvdroisoquinolin-l(2H)-one vial, 6-methoxy-3,4-dihydroisoquinolin-l(2H)-one (0.25 g, 1.411 mmol) was dissolved in N-dimethylformamide (2.82 ml). To this was added l-bromo-4-isobutylbenzene (0.451 g, 2.116 mmol) and potassium carbonate (0.390 g, 2.82 mmol). The reaction mixture was flushed with nitrogen, charged with copper(I) iodide (0.161 g, 0.847 mmol) and heated to 150 C for 24 h. The reaction mixture was cooled to room temperature, quenched with water and extracted three times with dichloromethane. The organic layers were combined, passed through a phase separator and concentrated. The crude material was purified via silica gel chromatography using 0-75% ethyl acetate in heptanes to afford the desired product (190 mg, 0.614 mmol, 43.5 % yield) as a light orange solid. NMR (400 MHz, Chloroform-d) delta 8.12 (d, J = 8.7 Hz, 1H), 7.32 – 7.27 (m, 2H), 7.24 – 7.15 (m, 2H), 6.89 (dd, J = 8.7, 2.6 Hz, 1H), 6.77 – 6.65 (m, 1H), 3.96 (dd, J = 7.0, 6.0 Hz, 2H), 3.86 (s, 3H), 3.09 (t, J = 6.4 Hz, 2H), 2.50 (d, J = 7.1 Hz, 2H), 1.90 (dh, J = 13.5, 6.8 Hz, 1H), 0.94 (d, J = 6.6 Hz, 6H). LC MS (m/z, MH+): 310.4., 22246-12-4

The synthetic route of 22246-12-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; NOVARTIS AG; BURKS, Heather Elizabeth; KARKI, Rajeshri Ganesh; KIRBY, Christina Ann; NUNEZ, Jill; PEUKERT, Stefan; SPRINGER, Clayton; SUN, Yingchuan; THOMSEN, Noel Marie-france; WO2015/92634; (2015); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

Downstream synthetic route of 22246-12-4

22246-12-4 6-Methoxy-3,4-dihydroisoquinolin-1(2H)-one 10607392, 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.22246-12-4,6-Methoxy-3,4-dihydroisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.

6-(Methyloxy)-3,4-dihydro-l(2H)-isoquinolinone (0.319 g, 1.8 mmol), ethyl-3- iodobenzoate (0.62 niL, 3.68 mmol), copper (I) iodide (0.044g, 0.23 mmol), potassium carbonate (0.247 g, 1.8 mmol) and lambda/,N-dimethylformamide (4 mL) were combined and the stirred reaction mixture was heated at 150 0C under nitrogen for 28 h. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give a gold-yellow liquid. The crude product was purified by flash chromatography over silica with a hexanes:ethyl acetate gradient (100:0 to 50:50) to give 0.32 g (55%) of ethyl 3-[6-(methyloxy)-l-oxo-3,4-dihydro-2(lH)- isoquinolinyl]benzoate as a clear colorless oil. 1H NMR (400 MHz; CDCl3): delta 8.10 (d, J = 9 Hz, IH), 8.00 (s, IH), 7.91 (d, J = 8 Hz, IH), 7.63 (d, J = 8 Hz, IH), 7.46 (t, J = 8 Hz, IH), 6.89 (dd, J = 9, 2 Hz, IH), 6.73 (d, J = 2 Hz, IH), 4.38 (q, J = 7 Hz, 2H), 4.01 (t, J = 6 Hz, 2H), 3.87 (s, 3H), 3.12 (t, J = 6 Hz, 2H), 1.38 (t, J = 7 Hz, 3H). ES- LCMS m/z 326(M + H)+., 22246-12-4

22246-12-4 6-Methoxy-3,4-dihydroisoquinolin-1(2H)-one 10607392, aisoquinoline compound, is more and more widely used in various fields.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/5998; (2009); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

Simple exploration of 22246-12-4

The synthetic route of 22246-12-4 has been constantly updated, and we look forward to future research findings.

To a solution of 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (31.3 g, 177 mmol) in CH2 Cl2 (300 mL) at -78 is added BBr3 (33.4 mL, 353 mmol). The reaction mixture is allowed to come to ambient temperature and is stirred for 12 hours. After this time the reaction mixture is cooled to 0 and is subsequently neutralized with 5N NaOH (150 mL) solution and saturated NaHCO3 solution. The resulting precipitate is extracted with hot acetone (4*500 mL) and the combined organics are concentrated in vacuo to give 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline.

The synthetic route of 22246-12-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Ciba-Geigy Corporation; US5334600; (1994); A;; ; Patent; Ciba-Geigy Corporation; US5260316; (1993); A;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem

Brief introduction of 22246-12-4

As the paragraph descriping shows that 22246-12-4 is playing an increasingly important role.

Example 5 (E)-methyl 3 -(4-(6-hydroxy-2-(4-isopropoxyphenyl)-l -methyl- 1.2.3.4-tetrahvdroisoquinolin-l- vD-phenvDacrylate 6-methoxy-3,4-dihydroisoquinolin-l(2H)-one (0.21 g, 1.185 mmol) was dissolved dichloromethane (5.93 ml). A I M solution of BBr3 (5.93 ml, 5.93 mmol) in heptanes was added dropwise and the reaction stirred for 30 min at rt. LC MS indicates the reaction was 50% complete, additional 1 M BBr3 in heptanes (5.93 ml, 5.93 mmol) was added. The reaction stirred for 1 h at rt. The reaction was then quenched with saturated sodium bicarbonate. The reaction was extracted with DCM but DCM extract did not contain any product. The product precipitated out on the reaction flask and was collected. The crude product was used without purification in the next reaction. NMR (400 MHz, DMSO-d6) delta 7.67 (d, J = 8.4 Hz, 1H), 6.69 (dd, J = 8.4, 2.4 Hz, 1H), 6.62 (d, J = 2.4 Hz, 1H), 3.31 (t, J = 6.1 Hz, 2H), 2.79 (t, J = 6.6 Hz, 2H). LC/MS (m/z, MH+): 164.1.

As the paragraph descriping shows that 22246-12-4 is playing an increasingly important role.