1,2-Dibromoethane → HCID 71468328, compound

Participants

Reaction Conditions

Reaction Steps

To solution containing (E)-tert-butyl 3-(3-(2-(3-hydroxybenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (67.3 mg, 0.15 mmol) and K2CO3 (40.13 mg, 0.29 mmol) dissolved in anhydrous acetonitrile (10.0 ml), 1,2-dibromoethane (0.0313 ml, 0.36 mmol) was added drop-by-drop. The reaction mixture was refluxed at 80° C. for 48 hr. After concentration under reduced pressure, the solution was separated through silica gel chromatography (n-hexane:EtOAc:methanol=10:3:1) so that ivory solid form of (E)-tert-butyl 3-(3-(2-(3-(2-bromoethoxy)benzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (15 mg, 18.1%). The resultant (E)-tert-butyl 3-(3-(2-(3-(2-bromoethoxy)benzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (15.0 mg, 0.026 mmol) and K2CO3 (7.27 mg, 0.053 mmol) were dissolved in anhydrous acetonitrile (10.0 ml) and the solution was drop-wise added with morpoline (0.01 ml, 0.053 mmol). The reaction mixture was refluxed at 85° C. for 12 hr. After concentration under reduced pressure, the solution was separated through silica gel chromatography (MC:methanol=24:1) so that ivory solid form of (E)-tert-butyl 3-(3-(1-isopropyl-2-(3-(2-morpholinoethoxy)benzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (10.6 mg, 69.9%).

Provenance & Evidence