Dimethylformamide → (1R,2R)-methyl-3-((-5'-fluoro-2-(4-iodophenyl)-2-isopropyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)benzoate

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C@:5]12[CH2:13][C@:12]1([C:17]1[CH:22]=[CH:21][C:20]([I:23])=[CH:19][CH:18]=1)[CH:14]([CH3:16])[CH3:15].[C:24]([O-:27])([O-])=O.[Cs+].[Cs+].CN([CH:33]=[O:34])C>>[CH3:24][O:27][C:33](=[O:34])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([CH2:5][N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[C@:5]3([CH2:13][C@:12]3([C:17]3[CH:18]=[CH:19][C:20]([I:23])=[CH:21][CH:22]=3)[CH:14]([CH3:16])[CH3:15])[C:6]2=[O:11])[CH:3]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 10796Cesium carbonate

HCID 58305290(1R,2R)-5'-fluoro-2-(4-iodophenyl)-2-isopropylspiro[cyclopropane-1,3'-indolin]-2'-one

Product 1

HCID 58305329(1R,2R)-methyl-3-((-5'-fluoro-2-(4-iodophenyl)-2-isopropyl-2'-oxospiro[cyclopropane-1,3'-indoline]-1'-yl)methyl)benzoateYield 92%

Procedure

(1S,2S) and (1R,2R)-5′-fluoro-2-(4-iodophenyl)-2-isopropylspiro[cyclopropane-1,3′-indolin]-2′-one (0.88 g, 2.1 mmol), methyl-(3-bromomethyl)-benzoate (725 mg, 3.15 mmol) and Cs2CO3 (1.37 g, 4.2 mmol) were mixed in anhydrous DMF and stirred at room temperature for 14 hours. The solvent was removed under reduced pressure. The residue was purified by flash column chromatography (gradient elution, 15-25% ethyl acetate in petroleum ether) to give the title product as white solid (1.10 g, 92%). LC/MS m/e calcd. for C28H25FINO: 569, observed (M+H)+: 570.1