Cesium fluoride → 4-(1,2-Dimethyl-1H-imidazol-5-yl)-2-methoxyaniline

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added 5-bromo-1,2-dimethyl-1H-imidazole (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): δ 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%].

Provenance & Evidence