Ethanol → HCID 21081639, compound

Participants

Reaction Conditions

Reaction Steps

A sealed tube was charged with a solution of 3-bromo-4-(2-fluoro-4-nitrophenoxy)-1-((2-(trimethylsilyl) ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (480 mg, 1.0 mmol) in toluene (5 mL), pyridin-4-ylboronic acid (246 mg, 2.0 mmol, Lancaster), 0.5 mL of ethanol, and potassium phosphate (1.0 mL, 2 M solution, 2.0 mmol). Argon was bubbled through the mixture for 15 minutes, and the reaction mixture was treated with tetrakis(triphenylphosphine)Pd(0)(58) mg, 0.05 mmol, Strem). the tube was sealed and the mixture was heated at 95 ° C. for 18 with vigorous stirring. The reaction mixture was then cooled to room temperature and diluted with EtOAc. The mixture ws washed with sasturated aq. NaHCO3 solution and brine, dried (MgSO4), and concentated in vacuo. The residue was purified by flash chromatography (SiO2, eluting with 2% MeOH in dichloromethane) to give the desired product (237 mg, 49%) as a thick brown oil. MS(ESI+) m/z 481.1 (M+H)+.

Provenance & Evidence