1H-Indole-3-propanoic acid → HCID 71468593, 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 (350 mg, 95%). In 2-neck round bottom flask, NaH (5.5 mg, 0.23 mmol) dissolved in DMF at 0° C. was stirred, and solution containing N′-(3-(1H-indol-3-yl)propanoyl)-N′-isopropylbenzohydrazide (20 mg, 0.06 mmol) dissolved in DMF was transported and stirred at 0° C. for 30. The reaction mixture was drop-wise added with (bromomethyl)benzene (0.01634 ml, 0.14 mmol), and stirred at 80° C. for 1 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=2:1) and dried so that ivory solid form of N′-(3-(1-benzyl-1H-indol-3-yl)propanoyl)-N′-isopropylbenzohydrazide was obtained (5 mg, 20%).

Provenance & Evidence