CCN=C=NCCCN(C)C.Cl.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[C:22]([OH:24])=O)[CH:15]=[CH:14]1.[C:25]([C:29]1[CH:30]=[CH:31][C:32]([CH2:36][NH:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)=[C:33]([OH:35])[CH:34]=1)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[C:25]([C:29]1[CH:30]=[CH:31][C:32]([CH2:36][N:37]([CH2:38][CH2:39][C:40]2[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=2)[C:22]([C:20]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:21]=2[NH:13][CH:14]=[CH:15]3)=[O:24])=[C:33]([OH:35])[CH:34]=1)([CH3:28])([CH3:26])[CH3:27]1.69 g (8.8 mmol) of EDC.HCl were added to 1.46 g (8.8 mmol) of 1H-indol-7-carboxylic acid and 2.41 g (8.8 mmol) of 5-tert-butyl-2-{[2-(4-fluoro-phenyl)-ethylamino]-methyl}-phenol dissolved in 80 ml DCM. The reaction mixture was stirred at rt over night, diluted with DCM and washed once with water and once with saturated aqueous NaCl solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (250 g silica gel; heptane/EtOAc 7:3) to yield 2.9 g (82%) 1H-indole-7-carboxylic acid (4-tert-butyl-2-hydroxy-benzyl)-[2-(4-fluoro-phenyl)-ethyl]-amide as a colorless foam. MS (ISP) 445.3 (M+H)+.
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