Iodobenzene → methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (441 mg, 0.76 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (279 mg, 0.30 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (16.600 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and then heated to 50ºC for 10 minutes. Cesium carbonate (6204 mg, 19.04 mmol), methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate (1700 mg, 7.62 mmol) and Iodobenzene (1.023 ml, 9.14 mmol) were stirred in anisole (33.2 ml), the flask was evacuated and flushed with nitrogen three times and then heated to 50ºC. The catalyst mixture was transferred into the flask with the reactants (by syringe) and the mixture heated to 100 °C for 18 hours. The reaction mixture was diluted with isohexane (60 ml) and the solid collected by filtration and washed with more isohexane (30 ml). The solid was slurried in DCM / MeOH and adsorbed onto silica then purified by flash silica chromatography eluting with 2% 3.7N NH3 / MeOH in DCM to give methyl 4-fluoro-1-methyl-5-(phenylamino)-1H-benzo[d]imidazole-6-carboxylate (1310 mg, 57.5 %) as a yellow solid.

Herkunft & Nachweise