N,N'-Dimethylethylenediamine → (1R,2R)-methyl-3-bromo-5-(2-(4-chlorophenyl)-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

A Schlenk tube charged with CuI (214 mg, 1.124 mmol, 20 mmol %), (1S,2S) and (1R,2R)-2-(4-chlorophenyl)spiro[cyclopropane-1,3′-indolin]-2′-one (1.50 g, 5.62 mmol) and K2CO3 (2.30 g, 16.86 mmol) was evacuated and backfilled with argon. N,N′-dimethylethylenediamine (242 μL, 2.25 mmol, 40 mol %), 3-Bromo-5-iodo-benzoic acid methyl ester (2.30 g, 6.75 mmol, 1.2 equiv.) and acetonitrile (5 mL) were added under argon. The Schlenk tube was sealed with a Teflon valve and the reaction mixture was stirred at 90° C. for 3 hours. HPLC monitor the reaction finished. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (gradient elution, 5-15% ethyl acetate in petroleum ether) to give the title compound as white powder (1.3 g, 48%). LC/MS m/e calcd. for C24H17BrClNO3: 482, observed (M+H)+: 483.

Provenance & Evidence