Water → HCID 69490095, compound

Participants

Reaction Steps

To a solution of 3370 mg (8.27 mmol) {2-[(5-Allyloxy-1H-indole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (36) in 100 ml methanol was added 5 ml water, 750 mg Pd (10% on C) and 300 mg p-toluenesulfonic acid. After heating at reflux for 6 h the reaction mixture was added to a 1:1 mixture of brine and saturated NaHCO3 solution. The aqueous phase was extracted twice with ethyl acetate and the combined organic phases were washed with brine, dried over Na2SO4 and filtrated over celite. The solvent was removed and the residue was subjected to silica gel chromatography (petrolether/ethyl acetate 2:1). {2-[(5-Hydroxy-1H-indole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (37) was recrystallized from diethyl ether/petrol ether to yield 1265 mg (3.44 mmol) crystalls, mp. 197° C. (decomposition).

Provenance & Evidence