Acetamide → HCID 89814421, compound

Participants

Reaction Conditions

Reaction Steps

Sparge a solution of 5-(7-chloro-2-ethyl-1,6-naphthyridin-3-yl)-2-fluoroaniline (0.63 g, 2.088 mmol) in dioxane (20 mL) with argon, add acetamide (0.987 g, 16.70 mmol), K3PO4 (1.773 g, 8.35 mmol), Pd2(dba)3 (0.096 g, 0.104 mmol) and BippyPhos (0.106 g, 0.209 mmol) and heat at 80° C. for 16 h. Cool to RT, remove the solids via filtration through diatomaceous earth, rinse well with EtOAc and H2O, and separate the layers of the filtrate. Extract the aqueous layer with EtOAc (1×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (250 mg, 37%) as an off-white solid. MS(ESI) m/z: 325.1 (M+H+).

Provenance & Evidence