Ammonium Chloride → HCID 59429706, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(6-chloro-3-dimethylaminomethyl-quinolin-5-yl)-acetamide (100 mg, 0.36 mmol) and (1H-indol-3-yl)-oxo-acetic acid methyl ester (110 mg, 0.54 mmol) in anhydrous THF was added dropwise a 1 M solution of t-BuOK in THF (1.8 mL) under an argon atmosphere at 0° C. The resulting deep red reaction mixture was stirred for 30 min. at 0° C., poured into a saturated aqueous NH4Cl solution and extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated at reduced pressure to afford an orange solid. Purification by size exclusion chromatography (Sephadex LH-20, MeOH afforded the title compound as an orange solid (88.3 mg, 0.205 mmol, 57%). 1H NMR (400 MHz, DMSO-d6, 298 K): δ=11.88 (bs, 1H), 11.25 (bs, 1H), 8.69 (d, J=1.9 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 8.02 (s, 1H), 7.91 (d, J=9.0 Hz, 1H), 7.85 (bs, 1H), 7.26 (d, J=8.1 Hz, 1H), 6.88 (t, J=7.4 Hz, 1H), 6.44 (t, J=7.4 Hz, 1H), 6.12 (d, J=8.1 Hz, 1H), 3.36 (AB-system: δA=3.48 (d, JAB=−13.2 Hz, 1H), δB=3.25 (d, JAB=−13.2 Hz, 1H)), 1.78 (s, 6H). MS (ES+): 431 (M(C24H1935ClN4O2)+H)+.

Provenance & Evidence