Ethyl isocyanate → 1-[3-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-3-ethyl urea

Participants

Reaction Conditions

Reaction Steps

2-(3-Aminophenylethynyl)-1-ethyl-6-methoxy-1H-indole-3-carbonitrile (100 mg, 0.32 mmol), prepared as described in Example 1H, was dissolved in pyridine (670 μL). Ethyl isocyanate (62 μL, 0.75 mmol) was added. The reaction mixture was then heated at 100° C. for 2 h. The mixture was then diluted in EtOAc, and was washed with aqueous HCl, followed by brine. The organic layer was dried and concentrated. Purification by silica chromatography (4/1, CH2Cl2/EtOAc), followed by trituration with hexanes/acetone (1/1), yielded 1-[3-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-ylethynyl)-phenyl]-3-ethyl urea (44 mg, 36%) as a white solid.

Provenance & Evidence