Diisopropylethylamine → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid N'-(thiophene-2-yl-aminocarbonyl) hydrazide

Participants

Reaction Conditions

Reaction Steps

DIPEA (53 μL, 0.31 mmol) and thienyl isocyanate (40 μL, 0.32 mmol) were added to a suspension of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid hydrazide trifluoroacetic acid salt (Preparation 10—route 1, 101 mg, 0.31 mmol) in a mixture of toluene and 1,4-dioxane (10 mL, 1:1). After stirring the mixture at 100° C. for 12 h, the reaction was allowed to cool to rt and the solvent was removed. The remaining oily residue was purified by flash chromatography on silica gel (toluene/acetone:2/1) to give the title compound. δH (CDCl3): 6.60 (1H, d), 6.78 (1H, m), 6.84 (1H, d), 7.26 (1H, d), 7.82 (1H, s), 8.61 (2H, m), 9.97 (1H, s); m/z (ES+)=336 [M+H]+; RT=2.97 min.

Provenance & Evidence