Dimethylamine → 1-Allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid dimethylamide

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Reaction Steps

To a solution of 1-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid (400 mg, 0.87 mmol, 1 equiv.) in 10 ml of DMF was added 0.22 mL of triethylamine (1.7 mmol, 2 equiv.) and PyBOP (500 mg, 0.96 mmol, 1.1 equiv.) followed by dimethylamine (2 M in THF, 1.3 mL, 2.6 mmol, 3 equiv.). After 18 hours, the mixture was diluted with 50 mL of brine and 50 mL of water and extracted with ethyl ether. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hexanes (10-60% gradient) to afford 354 mg (84%) of the title compound as a white solid. MS m/z 487.29 (MH+).

Provenance & Evidence