Category: 4885-18-1

Some common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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. Recommanded Product: 4885-18-1

Dimethylamine 49 (1.31 g, 6.13 mmol) was dissolved in anhydrous THF (15 ml) under Ar(g) in a flame-dried round-bottomed flask equipped with a reflux condenser. To facilitate generation of the Grignard reagent, a catalytic amount of 12 was added to the solution. Crushed magnesium turnings (223 mg, 9.2 mmol) were then added to this solution, and the resulting solution was heated at reflux for 2 hr to generate the Grignard reagent. In a separate flamed-dried flask, diethyl phosphite (237 mul, 1.84 mmol) was dissolved in anhydrous THF (1.0 ml), and cooled to 0 C. with an ice bath. The solution of Grignard reagent was added dropwise to this solution, and the resulting solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then quenched with water (1 ml), and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and the resulting solution was washed with water and brine. The combined organic extracts were dried over anhydrous MgSO4(s) and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, 20% v/v MeOH in CH2Cl2) to give phosphine oxide 50 as a colorless oil in 66% yield. 1H NMR (CDCl3, 400 MHz) delta 8.06 (d, J=1.2 Hz, 1H), 7.69 (s, 1H), 7.66 (s, 1H), 7.58 (t, J=7.5 Hz, 2H), 7.54 (dd, J=8.9, 1.2 Hz 2H), 7.45 (dd, J=7.6, 3.1 Hz 2H), 3.45 (s, 4H), 2.22 (s, 12H) ppm; 13C NMR (CDCl3, 100.6 MHz) delta 140.22 (d, J=10.7 Hz), 133.45, 132.15, 131.31 (d, J=12.2 Hz), 129.67 (d, J=11.2 Hz), 129.14 (d, J=12.2 Hz), 64.06, 45.58 ppm; 31P NMR (CDCl3, 161 MHz) delta 22.02 ppm; MS (ESI) m/z 288.0393 (MH+[C18H25N2OPH+]=288.0383).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Wisconsin Alumni Research Foundation; Raines, Ronald T.; Tam, Annie; Soellner, Matthew B.; US8410247; (2013); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, belongs to bromides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4885-18-1, Quality Control of 1-(3-Bromophenyl)-N,N-dimethylmethanamine

Example A135. (l R*.2S*)-2-(3-(3-((dimethylamino)methvnstyrvn-lH-indazol-6-yl)-5′- methoxyspiro[cyclopropane-l,3′-indolinl-2′-one 2,2,2-trifluoroacetate To a mixture of crude (l R*,2S*)-5′-methoxy-2-(3-vinyl-lH-indazol-6- yl)spiro[cyclopropane-l ,3′-indolin]-2′-one (100 mg, 0.2 mmol), l-(3-bromophenyl)-N,N- dimethylmethanamine (43 mg, 0.2 mmol), Pd(OAc)2 (2.2 mg, 0.01 mmol) and P(o-tol)3 (6.7 mg, 0.022 mmol) in DMF (2 mL) was added 1Pr2NEt (0.07 mL, 0.4 mmol). The resulting mixture was purged with argon, then microwaved 30 min at 125 0C. It was passed through a micro filter then purified by prep-HPLC to give the title compound as a light yellow solid. NMR indicated 7% branched isomer (43 mg, 37%). Spectral data was identical to that in obtained in Example A 134.

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Reference:
Patent; UNIVERSITY HEALTH NETWORK; SAMPSON, Peter Brent; Ll, Sze-Wan; LIU, Yong; PAULS, Heinz W.; EDWARDS, Louise G.; FORREST, Bryan T.; FEHER, Miklos; PATEL, Narendra Kumar B.; PAN, Guohua; WO2010/115279; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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. Computed Properties of C9H12BrN

Dimethylamine 49 (1.31 g, 6.13 mmol) was dissolved in anhydrous THF (15 ml) under Ar(g) in a flame-dried round-bottomed flask equipped with a reflux condenser. To facilitate generation of the Grignard reagent, a catalytic amount of 12 was added to the solution. Crushed magnesium turnings (223 mg, 9.2 mmol) were then added to this solution, and the resulting solution was heated at reflux for 2 hr to generate the Grignard reagent. In a separate flamed-dried flask, diethyl phosphite (237 mul, 1.84 mmol) was dissolved in anhydrous THF (1.0 ml), and cooled to 0 C. with an ice bath. The solution of Grignard reagent was added dropwise to this solution, and the resulting solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then quenched with water (1 ml), and the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2, and the resulting solution was washed with water and brine. The combined organic extracts were dried over anhydrous MgSO4(s) and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, 20% v/v MeOH in CH2Cl2) to give phosphine oxide 50 as a colorless oil in 66% yield. 1H NMR (CDCl3, 400 MHz) delta 8.06 (d, J=1.2 Hz, 1H), 7.69 (s, 1H), 7.66 (s, 1H), 7.58 (t, J=7.5 Hz, 2H), 7.54 (dd, J=8.9, 1.2 Hz 2H), 7.45 (dd, J=7.6, 3.1 Hz 2H), 3.45 (s, 4H), 2.22 (s, 12H) ppm; 13C NMR (CDCl3, 100.6 MHz) delta 140.22 (d, J=10.7 Hz), 133.45, 132.15, 131.31 (d, J=12.2 Hz), 129.67 (d, J=11.2 Hz), 129.14 (d, J=12.2 Hz), 64.06, 45.58 ppm; 31P NMR (CDCl3, 161 MHz) delta 22.02 ppm; MS (ESI) m/z 288.0393 (MH+[C18H25N2OPH+]=288.0383).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Wisconsin Alumni Research Foundation; Raines, Ronald T.; Tam, Annie; Soellner, Matthew B.; US8410247; (2013); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, 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. Computed Properties of C9H12BrN

A mixture of (3-bromo-benzyl)-dimethyl-amine (1.10 g; 5.14 mmol), ethyl acrylate (0.8 ml; 7.70 mmol), tri-o-tolyl-phosphane (156 mg; 0.53 mmol), Pd(OAc)2 (40 mg; 0.16 mmol) and NEt3 (1.4 ml; 10.0 mmol) is heated under reflux for 8 h. The reaction mixture is evaporated and the residue is subjected to flash chromatography on silica gel eluting with CH2Cl2/MeOH (95:5) to give the compound (800 mg; 3.43 mmol).

The synthetic route of 1-(3-Bromophenyl)-N,N-dimethylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; EP1598353; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4885-18-1, name is 1-(3-Bromophenyl)-N,N-dimethylmethanamine, molecular formula is C9H12BrN, 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. Safety of 1-(3-Bromophenyl)-N,N-dimethylmethanamine

(ii) 3-Bromo-N,N-dimethylbenzylamine (21.4 g) was reacted with magnesium turnings (2.4 g) in dry tetrahydrofuran (75 ml). The mixture was cooled to 0 and gaseous formaldehyde (generated by heating 15 g paraformaldehyde in a stream of argon) was passed over the stirred solution. Tetrahydrofuran (25 ml) was added and the mixture was stirred at room temperature for 2.5 hours and acidified to pH 1. The mixture was extracted with aqueous 3N hydrochloric acid, and the aqueous extracts were made alkaline with aqueous sodium hydroxide and extracted with ether. The ether extracts were evaporated to give 3-(dimethylaminomethyl)benzyl alcohol (14.78 g, 78%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4885-18-1, its application will become more common.

Reference:
Patent; Smith Kline & French Laboratories Limited; US4496567; (1985); A;,
Bromide – Wikipedia,
bromide – Wiktionary