Diethyl cyanophosphonate → (2-{4-[2-({5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-ethyl]-piperazin-1-yl}-1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a mixture of 5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-piperazin-1-yl-ethyl)-amide (150 mg, 0.24 mmol) and N-Boc D-alanine (19 mg, 1 eq.) in DCM (5 mL) cooled in an ice bath was added diethyl cyanophosphonate (48 mg, 1.2 eq.) in DCM (0.5 mL) followed by a dropwise addition of TEA (0.04 mL, 1 eq.) in DCM (0.5 mL). The mixture was then stirred at rt for overnight. The reaction was diluted with DCM, washed with 10% potassium carbonate, water, dried and concentrated to give (2-{4-[2-({5-[5-(2,6-dichloro-phenylmethanesulfonyl)-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carbonyl}-amino)-ethyl]-piperazin-1-yl}-1,1-dimethyl-2-oxo-ethyl)-carbamic acid tert-butyl ester as a red wax.

Provenance & Evidence