Oxalyl chloride → (2-{6-Chloro-3-[4-(2-oxo-2,3-dihydro-indol-1-yl)-piperidine-1-carbonyl]-indol-1-yl}-ethyl)-methyl-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of 0.20 g (0.57 mmol) 1-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-6-chloro-1H-indole-3-carboxylic acid, 0.11 ml (0.63 mmol) N,N-diisopropylethylamine and 2 drops of N,N-dimethylformamide in 4 ml dicholormethane were added 0.060 ml (0.74 mmol) oxalyl chloride at 0-5° C. After completed addition the reaction mixture was allowed to warm to room temperature and stirred for 3 h. A solution of 0.15 g (0.68 mmol) 1,3-dihydro-1-(piperidin-4-yl)-(2H)-indol-2-one and 0.11 ml (0.63 mmol) N,N-diisopropylethylamine in 2 ml dicholormethane was added. After stirring for 15 min at room temperature silica gel was added to the reaction mixture and the solvent was evaporated in vacuo. The residue was transferred to a silica gel column. Elution gave 0.26 g (82%) of the title compound as an off-white solid.

Provenance & Evidence