Dimethylamine → 6-Iodo-4-methoxy-quinoline-3-carboxylic acid dimethylamide

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Reaction Steps

To the mixture of 6-iodo-4-methoxy-quinoline-3-carboxylic acid (example 1b) (1.5 g, 4.56 mmol), 2 M dimethylamine in THF (tetrahydrofuran) (9.11 mL, 18.2 mmol), HOBt (0.74 g, 5.5 mmol) and DIEA (diisopropylethylamine) (2.38 mL, 13.7 mmol) in DMF (N,N-dimethylformamide) (40 mL) was slowly added the solution of O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU) (2.08 g, 5.47 mmol) in DMF (10 mL). After stirring at room temperature for 3 hours, the product was extracted with methylene chloride (2×100 mL). The combined organic layers were successively washed with a saturated aqueous sodium bicarbonate solution (3×50 mL) and water (3×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, using ethyl acetate as eluant) afforded 6-iodo-4-methoxy-quinoline-3-carboxylic acid dimethylamide (1.27 g, 78%) as a solid. LC-MS m/e 357 (MH+).

Provenance & Evidence