Category: 698-19-1

Synthetic Route of 698-19-1, A common heterocyclic compound, 698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

SYNTHESIS EXAMPLE 2 Preparation of Compound 4 Compound 2 (1.486 g, 5.04 mmol), 2-bromo-N-methylbenzylamine (0.74 mL, 5.00 mmol) and triethylamine (1.40 mL, 10.0 mmol) were dissolved in anhydrous dimethylformamide (10 mL) and placed in a pressure bottle, under an N2 atmosphere. The reaction was heated to 130 C. for 2 days. The reaction was cooled to room temperature and diluted into deionized water (250 mL). The suspension was basified to pH>9 with 1 N NaOH, and extracted twice with ethyl acetate. The combined ethyl acetate extracts were dried over Na2SO4, filtered through a pad of silica gel (ethyl acetate), and dried under vacuum. The crude product was dissolved in ethyl acetate and minimal methanol and adhered to silica gel (25 g). The silica adhered compound was purified by flash silica gel chromatography (250 g silica, 3:1 hexanes:ethyl acetate) to yield 1.74 g (84%) of 4 as a white solid. ESI-MS m/z 414.1/416.1 [M+H]+. Analalysis: Calcd for C20H17BrFN3O: C, 57.98; H, 4.14; N, 10.14. Found: C, 58.08; H, 4.20; N, 10.02. 1H NMR (500 MHz, DMSO-d6) delta 10.06 (s, 1H), 8.69 (d, J=2.3 Hz, 1H), 8.09 (dd, J=9.0 Hz, 2.3 Hz, 1H), 7.77-7.74 (m, 2H), 7.68 (d, J=8.0 Hz, 1H), 7.33 (t, J=7.5 Hz, 1H), 7.22 (t, J=7.8 Hz, 1H), 7.18 (t, J=9.0 Hz, 2H), 6.99 (d, J=7.5 Hz, 1H), 6.78 (d, J=9.4 Hz, 1H), 4.89 (s, 2H), 3.20 (s, 3H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Syntrix Biosystems Inc.; US2012/46243; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, molecular formula is C8H10BrN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Formula: C8H10BrN

To a stirred solution of commercially available1-(2-bromophenyl)-N-methylmethanamine (565 mg, 2.8 mmol, 1.0 equiv.) and propiolic acid (0.21 mL,3.4 mmol, 1.2 equiv.) in CH2Cl2 (30 mL) was added DCC (700 mg, 3.4 mmol, 1.2 equiv.) at 0 C.Then, the reaction temperature was raised to r.t. After 1.5 h, the reaction mixture was diluted withCH2Cl2 (200 mL), and then washed with aq. 2N-HCl (5 mL) and sat. aq. NaHCO3 (20 mL). The organiclayer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude residue waspurified by column chromatography (silica gel, hexanesEtOAc 3:1) to yield 6c (675 mg, 95% yield) asan off-white solid; m.p. = 53.1 C; Rf = 0.3 (silica gel, hexanesEtOAc 2:1); IR (film) 3283, 3215, 3061,2926, 2107, 1644, 1401 cm-1; 1H-NMR (CDCl3, 1.3:1 atropisomeric mixture): delta = 7.59 (d, J = 8.0 Hz,1H, major), 7.56 (d, J = 8.0 Hz, 1H, minor), 7.35 (t, J = 7.5 Hz, 1H, major), 7.30 (t, J = 7.5 Hz, 1H, minor),7.19 (t, J = 7.8 Hz, 2H, major), 7.16 (d, J = 7.8 Hz, 2H, minor), 4.91 (s, 2H, major), 4.75 (s, 2H, minor),3.09 (s, 1H, major), 3.20 (s, 1H, minor), 2.94 (s, 3H, major), 3.18 (s, 3H, minor), ppm; 13C-NMR (CDCl3): delta= 154.4 (major), 154.2 (minor), 135.3 (major), 135.3 (minor), 133.5 (major), 133.3 (minor), 129.8 (major),129.6 (minor), 129.5 (minor), 128.4 (major), 128.3 (major), 128.2 (minor), 80.0 (minor), 79.4 (major),76.0 (minor), 75.9 (major), 54.9 (major), 50.0 (minor), 36.5 (minor), 32.7 (major) ppm; HRMS (EI): calcd. forC23H18ClNO [M+]: 250.9946, found 250.9944.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 698-19-1, its application will become more common.

Reference:
Article; Park, Sunhwa; Lee, Jiyun; Shin, Kye Jung; Oh, Euichaul; Seo, Jae Hong; Bunce, Richard A.; Molecules; vol. 22; 3; (2017);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 698-19-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 698-19-1 name is 1-(2-Bromophenyl)-N-methylmethanamine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Preparation of ferf-butyl 2-bromobenzyl(methyl)carbamate (59). 58 59 A solution of compound 58 (2.0 g, 10.0 mmol) and Boc20 (2.29 g, 10.5 mmol) in THF (40 mL) was stirred at RT for 16 hours. The mixture was then concentrated in vacuo. The crude product was purified by flash column chromatography over silica gel, which was eluted with 10% EtOAc in heptanes, and yielded compound 59 as a colorless oil (2.8 g, 95% yield). 1H NMR (400 MHz, CDCI3) delta 7.54 (d, 1 H), 7.30 (t, 1 H), 7.13 (m, 2 H), 4.53 (br d, 2 H), 2.87 (br s, 3 H), 1.46 (br d, 9 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromophenyl)-N-methylmethanamine, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 1-(2-Bromophenyl)-N-methylmethanamine

A mixture of compound 1A (4.30 g), [N-Boc-glycine] (3.01 g, 17.1 mmol), EDC (3.28 g, 17.1 mmol), and HOAt (2.34 g, 17.1 mmol) in DCM (50 ml) was stirred at rt overnight. The reaction was quenched with the addition of sat’d NaHCO3 solution. The organic layer was separated, washed with brine, dried MgSO4), and concentrated to give the crude product which was purified by flash chromatography (10-20% EtOAc/ hexane) to give compound 1B (3.35 g) as a colorless film.

The synthetic route of 698-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2004/788; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 698-19-1

General procedure: To an oven dried Schlenk tube, were added amine 2 (1 mmol) and alkyl (ethyl or methyl or tert-butyl) acrylate (5 mmol) at room temperature under nitrogen atmosphere. The reaction mixture was stirred at 110 C in an oil bath, for 24 h (in case of methyl as well as ethyl acrylates) and for 48 h (in case of tert-butyl acrylate). Progress of the Michael addition was monitored by TLC. The reaction mixture was allowed to attain room temperature, and excess of alkyl acrylate was removed under vacuum (10-2 mbar). To the resultant reaction intermediate (i.e., Michael addition product 3) at room temperature, were added Pd(OAc)2 (10 mol %), PPh3 (20 mol %), and Cs2CO3 (2 mmol) followed by toluene (3 mL) under nitrogen atmosphere. The reaction mixture was then allowed to stir at 80 C for 24 h (in case of 4a-c and 4f), 36 h (in case of 4d, 4e, 4g, 4i, 4j and 4l-n), and 48 h (in case of 4h and 4k) in an oil bath and the progress was monitored by TLC. The mixture was cooled to room temperature, treated with aqueous NH4Cl solution and then extracted with ethyl acetate (3×15 mL). The organic layer was washed with saturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reduced pressure and purification of the crude material by silica gel column chromatography (petroleum ether/ethyl acetate) furnished the tetrahydroisoquinoline 4 (70-85%).

The synthetic route of 698-19-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, Alavala Gopi Krishna; Satyanarayana, Gedu; Tetrahedron; vol. 68; 38; (2012); p. 8003 – 8010;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 698-19-1, These common heterocyclic compound, 698-19-1, name is 1-(2-Bromophenyl)-N-methylmethanamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of compound 1A (1.0 g, 5 mmol) in 50 mL of DCM was added N-Boc-glycine (950 mg, 5.4 mmol), followed by [1-HYDROXY-7-AZABENZOTRIAZOLE] (800 mg, 5.84 mmol) and [1- (3-DIMETHYLAMINOPROPYL)-3-ETHYLCARBODIIMIDE] hydrochloride (4.41 g, 7.38 mmol). The reaction mixture was stirred at rt for 4 hours and concentrated under reduced pressure. The resulting oil was dissolved in EtOAc and washed successively with saturated sodium bicarbonate, 1N-hydrochloric acid, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (1.8 g, 99%) as a colorless oil, which was used for the subsequent step without further purification

Statistics shows that 1-(2-Bromophenyl)-N-methylmethanamine is playing an increasingly important role. we look forward to future research findings about 698-19-1.

Reference:
Patent; Bristol-Myers Squibb Company; WO2004/214; (2003); A2;,
Bromide – Wikipedia,
bromide – Wiktionary