2-Methoxy-5-nitroaniline → 5-chloro-4-(1H-indol-3-yl)-N-(2-methoxy-5-nitrophenyl)pyrimidin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-(2,5-dichloropyrimidin-4-yl)-1H-indole (100 mg, 0.38 mmol) in dioxane (10 mL) was added 2-methoxy-5-nitroaniline (63.7 mg, 0.38 mmol), cesium carbonate (247 mg, 0.76 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (26.3 mg, 0.05 mmol). The resulting suspension was purged with nitrogen for 5 minutes. diacetoxypalladium (5.10 mg, 0.02 mmol) was added and the mixture was purged with nitrogen for a further 5 minutes, and then heated at 80 °C overnight. UPLC shows di-Cl SM almost completely consumed but no evidence of desired product. Reaction stopped

Provenance & Evidence