Category: 115929-62-9

Electric Literature of 115929-62-9, These common heterocyclic compound, 115929-62-9, name is 3-Bromo-2,5-dimethoxyaniline, 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.

General procedure: In a round bottom flask equipped with a magnetic stirring bar, 0.3mmol of alpha-formyl-beta-carboline (1a) and 0.3mmol of aniline (2a) in 4mL of [Bmim][BF4] was stirred for 12min. Into this reaction mixture were added 0.35mmol of phenylacetylene (3a) and 10mol% of La(OTf)3 and then heated around 95-100C. After completion of the reaction, as indicated by the TLC, water was added and extracted with ethylacetate. The organic layer was dried over anhydrous Na2SO4. The solvent was concentrated under the reduced pressure. Product was purified by column chromatography on silica gel (eluent: Hexanes/ethyl acetate): Colorless solid, 126 mg, 74%, Rf=0.52 (20% EtOAc/Hexanes), mp: 277-279 C; IR (KBr): 3356, 2939, 2841, 1259, 1107, 744, 545 cm-1; 1H NMR (400 MHz, CDCl3, TMS) delta: 12.51 (1H, s), 9.01 (1H, s), 8.77 (1H, s), 8.28 (1H, d, J=7.7 Hz), 7.76-7.78 (1H, m), 7.69 (1H, t, J=7.4 Hz), 7.40-7.45 (6H, m), 6.99 (1H, s), 4.31 (3H, s), 4.08 (3H, s), 3.56 (3H, s); 13C NMR (100 MHz, CDCl3, TMS) delta: 166.7, 156.3, 153.2, 149.7, 147.2, 143.3, 141.9, 141.3, 137.3, 137.2, 136.9, 130.8, 129.2, 128.3, 127.2, 127.1, 122.1, 121.6, 121.3, 120.9, 119.0, 118.9, 116.7, 112.3, 110.3 (aromatic C), 61.6, 55.7, 52.6 (aliphatic C); HRMS (ESI-MS) calcd for C30H22BrN3O4; 590.0692 (M+Na), found: 590.0692. Anal. Calcd for: C, 63.39; H, 3.90; N, 7.39%; found: C, 63.25; H, 3.98; N, 7.21%.

Statistics shows that 3-Bromo-2,5-dimethoxyaniline is playing an increasingly important role. we look forward to future research findings about 115929-62-9.

Reference:
Article; Ramesh, Subburethinam; Nagarajan, Rajagopal; Tetrahedron; vol. 69; 24; (2013); p. 4890 – 4898;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 115929-62-9, These common heterocyclic compound, 115929-62-9, name is 3-Bromo-2,5-dimethoxyaniline, 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.

General procedure: In a round bottom flask equipped with a magnetic stirring bar, 0.3mmol of alpha-formyl-beta-carboline (1a) and 0.3mmol of aniline (2a) in 4mL of [Bmim][BF4] was stirred for 12min. Into this reaction mixture were added 0.35mmol of phenylacetylene (3a) and 10mol% of La(OTf)3 and then heated around 95-100C. After completion of the reaction, as indicated by the TLC, water was added and extracted with ethylacetate. The organic layer was dried over anhydrous Na2SO4. The solvent was concentrated under the reduced pressure. Product was purified by column chromatography on silica gel (eluent: Hexanes/ethyl acetate): Colorless solid, 126 mg, 74%, Rf=0.52 (20% EtOAc/Hexanes), mp: 277-279 C; IR (KBr): 3356, 2939, 2841, 1259, 1107, 744, 545 cm-1; 1H NMR (400 MHz, CDCl3, TMS) delta: 12.51 (1H, s), 9.01 (1H, s), 8.77 (1H, s), 8.28 (1H, d, J=7.7 Hz), 7.76-7.78 (1H, m), 7.69 (1H, t, J=7.4 Hz), 7.40-7.45 (6H, m), 6.99 (1H, s), 4.31 (3H, s), 4.08 (3H, s), 3.56 (3H, s); 13C NMR (100 MHz, CDCl3, TMS) delta: 166.7, 156.3, 153.2, 149.7, 147.2, 143.3, 141.9, 141.3, 137.3, 137.2, 136.9, 130.8, 129.2, 128.3, 127.2, 127.1, 122.1, 121.6, 121.3, 120.9, 119.0, 118.9, 116.7, 112.3, 110.3 (aromatic C), 61.6, 55.7, 52.6 (aliphatic C); HRMS (ESI-MS) calcd for C30H22BrN3O4; 590.0692 (M+Na), found: 590.0692. Anal. Calcd for: C, 63.39; H, 3.90; N, 7.39%; found: C, 63.25; H, 3.98; N, 7.21%.

Statistics shows that 3-Bromo-2,5-dimethoxyaniline is playing an increasingly important role. we look forward to future research findings about 115929-62-9.

Reference:
Article; Ramesh, Subburethinam; Nagarajan, Rajagopal; Tetrahedron; vol. 69; 24; (2013); p. 4890 – 4898;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem