Tetrahydrofuran → 5-[6-(1-{[tert-Butyl(dimethyl)silyl]oxy}-1-methylethyl)pyridin-3-yl]-2-nitrothiophene-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-nitrothiophene-3-carboxamide (602 mg, 2.40 mmol), 2-(1-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (905 mg, 2.40 mmol), and Pd(PPh3)4 (139 mg, 0.12 mmol) were combined in a vial and evacuated/backfilled with nitrogen. THF (5.6 mL) and 2 N Na2CO3 (2.4 mL) were added, and the reaction was stirred at 90° C. overnight. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography of the crude residue (10-100% EtOAc/hexanes) afforded the title compound as a yellow solid.

Provenance & Evidence