Sodium Carbonate → HCID 59526292, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-2-nitrothiophene-3-carboxamide (Intermediate 10, Step 4) (1.44 g, 5.74 mmol), 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxetan-3-ol (1.821 g, 6.60 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.331 g, 0.287 mmol) were taken up in THF (25 mL)/2 N Na2CO3 (10 mL) and the reaction mixture was stirred at 80° C. overnight. After cooling to room temperature, saturated NH4Cl and EtOAc were added. The resulting precipitate was collected by filtration, washed with water and dried to give 5-[4-(3-hydroxyoxetan-3-yl)phenyl]-2-nitrothiophene-3-carboxamide as a brown solid (batch 1). The organic phase from the filtrate was separated, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo while loading onto silica. Purification of the residue by flash silica gel column chromatography (12-100% EtOAc-hexanes followed by 0-10% MeOH-EtOAc) gave the title compound as an orange solid after recrystallising from EtOH (batch 2).

Provenance & Evidence