| 99% |
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 150℃; for 0.166667h;Microwave irradiation; |
Preparation 53 (1154) -(1 ,2-dimethyl-1 /-/-imidazol-5-yl)-2-methoxyaniline (1155) (1156) A suspension of 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (925 mg, 3.71 mmol), 5-bromo-1 ,2-dimethylimidazole (650 mg, 3.71 mmol), CsF (1 .7 g, 1 1 .14 mmol) and Pd(PPh3)4 (86 mg, 0.074 mmol) in DME/MeOH (2:1 , 18 mL) was heated to 1 50C for 10 minutes under microwave irradiation. The reaction mixture was diluted with EtOAc and water. The aqueous layer was basified by addition of 2M aqueous Na2C03 and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgS04) and concentrated in vacuo. The residue was purified by reverse phase column chromatography eluting with 1 00% water to afford the title compound (800 mg, 99%). (1157) 1 H NMR (500 MHz, MeOH-d4) delta ppm 6.84 (d, J = 2.0 Hz, 1 H), 6.81 (s, 1 H), 6.78 (d, J = 2.0 Hz, 1 H), 6.75 (s, 1 H), 3.88 (s, 3H), 3.53 (s, 3H), 2.41 (s, 3H). (1158) HRMS (ESI) MS m/z calcd for C12H16N3O [M+H]+ 218.1288 , found 21 8.1200. |
| 42% |
With cesium fluoride;tetrakis(triphenylphosphine) palladium(0); In methanol; 1,2-dimethoxyethane; at 150℃; for 1h;Microwave irradiation; |
Preparation 95: 4-(1 ,2-Dimethyl-1 H-imidazol-5-yl)-2-methoxyaniline; [00265] To a microwave vial was added 5-bromo-1 ,2-dimethyl-1 /-/-imidazole (230mg, 1 .31 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (393mg, 1 .58mmol), Pd(PPh3)4 (152mg, 0.13mmol), CsF (599mg, 3.94mmol) and DME/MeOH 3/1 (4ml_). The mixture was heated in a microwave at 150C for 1 hour. The reaction mixture was then filtered and concentrated onto silica gel and purified by Biotage silica gel column chromatography eluting with (EtOAc/MeOH 100/0 to 96/4) to give the title product as a light brown oil (120mg, 42 %). 1 H NMR (500 MHz, CDCI3): delta 2.43 (s, 3H), 3.48 (s, 3H), 3.87 (s, 3H), 6.73-6.78 (m, 3H), 6.87 (s, 1 H). LC (Method A)-MS (ESI, m/z) tR 0.49 min, 218 [(M+H+), 100%]. |
| 42% |
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride; In methanol; 1,2-dimethoxyethane; at 150℃; for 1h;Microwave irradiation; |
Preparation 95 4-(1,2-Dimethyl-1H-imidazol-5-yl)-2-methoxyaniline To a microwave vial was added <strong>[24134-09-6]5-bromo-1,2-dimethyl-1H-imidazole</strong> (230 mg, 1.31 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (393 mg, 1.58 mmol), Pd(PPh3)4 (152 mg, 0.13 mmol), CsF (599 mg, 3.94 mmol) and DME/MeOH 3/1 (4 mL). The mixture was heated in a microwave at 150 C. for 1 hour. The reaction mixture was then filtered and concentrated onto silica gel and purified by Biotage silica gel column chromatography eluting with (EtOAc/MeOH 100/0 to 96/4) to give the title product as a light brown oil (120 mg, 42%). 1H NMR (500 MHz, CDCl3): delta 2.43 (s, 3H), 3.48 (s, 3H), 3.87 (s, 3H), 6.73-6.78 (m, 3H), 6.87 (s, 1H). LC (Method A)-MS (ESI, m/z) tR 0.49 min, 218 [(M+H+), 100%]. |
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
