Chlorosuccinimide → (2-Amino-5-chloro-thiophen-3-yl)-(4-fluoro-phenyl)-methanone
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8].[Cl:16]N1C(=O)CCC1=O>ClCCl>[NH2:1][C:2]1[S:3][C:4]([Cl:16])=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 0.26 g (1.18 mmol) (2-amino-thiophen-3-yl)-(4-fluoro-phenyl)-methanone (the preparation of which is described in example 22) in 10 ml dichloromethane at 0° C. was added 164 mg (1.18 mmol) N-chloro-succinimide (NCS). The mixture was then stirred from 0° C. to RT over night, and then poured onto water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentratedin vacuo. Flash chromatography (heptane/ethyl acetate 4:1) afforded 95 mg (32%) (2-amino-5-chloro-thiophen-3-yl)-(4-fluoro-phenyl)-methanone as a yellow solid. ES-MS m/e (%): 256 (M+H+, 100).