Methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoate → HCID 53794293, compound
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][C:21]=1[C:22]#[C:23][CH2:24][CH2:25][CH3:26])[C:15]([O:17][CH3:18])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Cl-].[Na+].[Au+3].[Cl-].[Cl-].[Cl-]>[CH2:1]([O:8][C:9]([N:11]1[C:12]2[C:21](=[CH:20][CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH:22]=[C:23]1[CH2:24][CH2:25][CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of methyl 3-benzyloxycarbonylamino-4-(1-pentynyl)benzoate (949 mg) in tetrahydrofuran (24 ml) was added gold(III)sodium chloride (24 mg) under argon atmosphere, and the mixture was heated under reflux for 100 minutes. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel eluting with a mixture of hexane, dichloromethane, and ethyl acetate (6:3:2) to give methyl 1-benzyloxycarbonyl-2-propylindole-6-carboxylate (852 mg) as colorless crystals.