2-Morpholinoethanol → {2-dimethylcarbamoyl-6-fluoro-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-carbamic acid 2-morpholin-4-yl-ethyl Ester

Participants

Reaction Steps

75 mg (0.13 mmol) of 3-fluoro-2-isocyanato-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide was dissolved in 1.0 mL dichloromethane and combined with 31 μL (0.26 mmol) of 4-(2-hydroxyethyl)-morpholine (which was dried over molecular sieves) and 22 μL (0.13 mmol) of N,N-diisopropylethylamine. The reaction was stirred for 16 hours at room temperature. 31 μL (0.26 mmol) of 4-(2-hydroxyethyl)morpholine was added and the reaction was continued to stir for 24 hours at room temperature. The reaction was concentrated and purified by flash chromatography on silica gel using a gradient of ethyl acetate (containing 10% methanol) and hexanes. The clean fractions were concentrated. MS: m/z 715.3 (M+H+).

Provenance & Evidence