[H-].[Na+].[CH2:3]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22].O>CN(C=O)C>[CH2:3]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1To a suspension of NaH (50% dispersion in oil, 170 mg, 3.5 mmol) in DMF (15 mL), at r.t. and under an atmosphere of nitrogen, there was added in portions 3-benzylindole (ref: Tetrahedron 23, 3771-83 (1967)) (621 mg, 3 mmol) and the mixture was stirred for 1 hour. There added methyl bromoacetate (765 mg, 5 mmol) and stirring was continued for 1.5 hours. H2O (100 mL) was added and the mixture was extracted twice with Et2O. These extracts were H2O with water, dried over MgSO4 and evaporated to a residue which was chromatographed on silica gel eluting with a 1:5 mixture of EtOAc acetate and hexane to afford the title product as an oil.
Wird geladen…
