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

反応式

[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

参加物

反応物 3

HCID 6228Dimethylformamide

HCID 10796Cesium carbonate

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

生成物 1

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

実験手順

(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