Aniline → HCID 178509226, compound

Participants

Reaction Steps

Aniline (0.035 mL, 0.386 mmol), Pd2 dba3 (0.024 g, 0.0257 mmol), Xantphos (0.030 g, 0.0714 mmol), K3PO4 (0.120 g, 0.566 mmol) was added to a suspension of 3-bromo-5-nitro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridine (0.096 g, 0.257 mmol) in toluene (10 mL), and the mixture was heated to reflux overnight. The reaction mixture was cooled to room temperature and filtered through celite. The filter cake was washed with ethyl acetate. The combined filtrate was concentrated to give the crude product 5-nitro-N-phenyl-1-(2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-b]pyridin-3-amine. This material was used without purification in the next step.

Provenance & Evidence