1H-Indole-3-propanoic acid → HCID 71468596, compound

Participants

Reaction Steps

To solution containing 3-(1H-indol-3-yl)propanoic acid (200 mg, 1.06 mmol), N′-isopropylbenzohydrazide (283.4 mg, 1.59 mmol) and HATU (604.6 mg, 1.59 mmol) dissolved in DMF (7.0 ml), N,N-diisopropylethylamine (DIPEA)(0.277 ml, 1.59 mmol) was slowly drop-wise added and stirred at room temperature for 12 hr. The reaction mixture was diluted with EtOAc, washed with water and brine, dried with anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was separated through silica gel chromatography (n-hexane:EtOAc:methanol=20:3:1) and dried so that white solid form of N′-(3-(1H-indol-3-yl)propanoyl)-N′-isopropylbenzohydrazide was obtained. After adding K2CO3 to N′-(3-(1H-indol-3-yl)propanoyl)-N′-isopropylbenzohydrazide, nitrogen substitution, and dissolving in THF/H2O, (Boc)2O was slowly drop-wise added and refluxed for 12 hr. After the reaction mixture was concentrated under reduced pressure, the residue was separated through silica gel chromatography (n-hexane:EtOAc:methanol=15:3:1) and dried so that white solid form of tert-butyl 3-(3-(2-benzoyl-1-isopropylhydrazinyl)-3-oxopropyl)-1H-indole-1-carboxylate was obtained. (285.9 mg, 60%)

Provenance & Evidence