2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → (R)-N-(6-Methylthioquinolin-5-yl)-2-bromodecanoic amide

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Reaction Steps

(R)-2-Bromodecanoic acid (210 mg, 0.83 mmol), 5-amino-6-methylthioquinoline (160 mg, 0.84 mmol) and 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ, 223 mg, 0.90 mmol) were stirred in 6 ml of toluene at 0° C. The reaction was allowed to warm to rt and stirred under N2 for 18 hours. The reaction was quenched with 100 ml of 10% citric acid and extracted with ethyl acetate (3×50 ml). The organic phase was washed with 0.5N NaHCO3, brined and dried over Na2SO4. Purification by silica gel column chromatography (eluent: 100% CHCl3) yielded 120 mg (34% yield) of the desired product: 1H NMR (CDCl3) δ8.85 (1H, d, J=3 Hz), 8.09 (1H, d, J=9 Hz), 8.08 (1H, d, J=9 Hz), 7.98 (1H, bs), 7.65 (1H, d, J=9 Hz), 7.42 (1H, dd, J=9, 9 Hz), 4.61 (1H, dd, J=8, 8 Hz), 2.58 (3H, s), 2.33 (1H, m), 2.21 (1H, m), 1.76-121 (12H, m), 0.88 (3H, m).

Provenance & Evidence