1,2-Dibromoethane → HCID 71468329, compound

Participants

Reaction Conditions

Reaction Steps

(E)-tert-butyl 3-(3-(2-(4-hydroxybenzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (50.0 mg, 0.11 mmol) and K2CO3 (59.63 mg, 0.43 mmol) dissolved in anhydrous acetonitrile (10.0 ml), 1,2-dibromoethane (0.0465 ml, 0.54 mmol) was added drop-by-drop. The reaction mixture was refluxed at 85° C. for 48 hr. After concentration under reduced pressure, the solution was separated through silica gel chromatography (n-hexane:EtOAc:methanol=14:3:1) so that ivory solid form of (E)-tert-butyl 3-(3-(2-(4-(2-bromoethoxy)benzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained.(34 mg, 55.3%). The resultant (E)-tert-butyl 3-(3-(2-(4-(2-bromoethoxy)benzoyl)-1-isopropylhydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (34.0 mg, 0.06 mmol) and K2CO3 (16.5 mg, 0.12 mmol) were dissolved in anhydrous acetonitrile (10.0 ml), and the solution was drop-wise added with morpholine (0.01031 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=30:1) so that ivory solid form of (E)-tert-butyl3-(3-(1-isopropyl-2-(4-(2-morpholinoethoxy)benzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (8.2 mg, 23.9%).

Provenance & Evidence