2-Fluoro-4-nitrophenol → 3-Fluoro-4-(2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzenamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (3.2 g, 8.9 mmol), 2-fluoro-4-nitrophenol (2.79 g, 17.8 mmol), and DIPEA (3.5 mL, 20 mmol) in NMP (15 mL) was heated in a sealed tube at 185° C. for 3 days. The mixture was diluted with EtOAc and filtered through a short pad of Celite® (EtOAc). The filtrate was washed with 5% aq. Na2CO3 solution and dried over MgSO4. The title compound was purified by flash column chromatography (silica gel, 100% CH2Cl2 to 50% EtOAc/CH2Cl2) to afford the desired product (295 mg, 7.4%) as a light brown solid. LC/MS(ESI+) m/z 451 (M+H)+.

Provenance & Evidence