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

참여 물질

반응 조건

반응 단계

9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (389 mg, 0.67 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (246 mg, 0.27 mmol) were added to a round bottom flask which was evacuated and flushed with nitrogen 3 times, anisole (14.900 ml) was added and the mixture evacuated and flushed with nitrogen 3 times and then heated to 50ºC for 10 minutes. Cesium carbonate (5474 mg, 16.80 mmol), methyl 5-amino-4-fluoro-1-methyl-1H-benzo[d]imidazole-6-carboxylate (1500 mg, 6.72 mmol) and Iodobenzene (0.902 ml, 8.06 mmol) were stirred in anisole (29.800 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 (50 m) and the solid collected by filtration and washed with more isohexane (25 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 (1510 mg, 75 %) as a light yellow solid.

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