Potassium Hydroxide → N-{6-[6-Methoxy-7-(2-pyrrolidin-1-yl-ethoxy)-quinolin-4-yloxy]-naphthalen-1-yl}-benzamide

Participants

Reaction Conditions

Reaction Steps

To a microwaveable vial containing 0.300 g (0.0011 mmol) of N-(6-hydroxy-naphthalen-1-yl)-benzamide in 1.5 mL DMF and 1.5 mL pyridine, was added 0.858 g (0.0028 mmol) of 4-chloro-6-methoxy-7-(2-pyrrolidin-1-yl-ethoxy)-quinoline. Copper grind was added (5 mmol %) to the mixture, along with 0.158 g (0.0025 mmol) KOH pellets. The vial was heated in a microwave for 18 min at 120° C., (60 Watts of constant power, powermax, CEM). The mixture was diluted with CH2Cl2 and water, then transferred to a seperatory funnel. The organics were extracted 3× with CH2Cl2. Then combined all organics, dried over Na2SO4, filtered, and concentrated in-vacuo. The crude was purified by reverse-phase HPLC. A tan oil was collected, which was the titled product. MS (ESI pos. ion) m/z: 534 (M+H). Calc'd for C33H31N3O4−533.23.

Provenance & Evidence