[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8].[Br:15]N1C(=O)CCC1=O.[C:23]([O:26]C(=O)C)(=O)[CH3:24].CCN(CC)CC>CN(C1C=CN=CC=1)C>[C:7]([C:6]1[CH:5]=[C:4]([Br:15])[S:3][C:2]=1[NH:1][C:23](=[O:26])[CH3:24])(=[O:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
To a stirred solution of 1.00 g (4.92 mmol) of (2-amino-thiophen-3-yl)-phenyl-methanone (the preparation of which is described in example 20) in 20 ml CFCl2 at 0° C. was added 0.92 g (5.18 mmol) NBS (N-bromo succinimide) in one portion. After 10 minutes, 4.65 ml (49.2 mmol) of acetic anhydride, 0.68 ml (4.92 mmol) of Et3N and 0.30 g (2.45 mmol) of DMAP were added. Stirring was continued at RT for 2 hours, the mixture was poured onto water and extracted three times with CH2Cl2. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/CH2Cl2 1:1) afforded 0.85 g (53%) N-(3-benzoyl-5-bromo-thiophen-2-yl)-acetamide as a light brown solid. ES-MS m/e (%): 324, 326 (M+H+, 100).
Wird geladen…
