B(Br)(Br)Br.Cl.[N:6]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[C@@H:8]([NH:14][C:15]([C:17]1S[C:19]3[C:25]([C:26]4C=C([CH:32]=[CH:33][CH:34]=4)C(O)=O)=[CH:24][CH:23]=[CH:22][C:20]=3[CH:21]=1)=O)[CH2:7]2.C([O:37][CH2:38][CH3:39])C.[OH-:40].[Na+].[OH2:42]>ClCCl>[N:6]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[C@@H:8]([NH:14][C:15]([C:17]1[O:42][C:19]3[C:25]([C:26]4[CH:34]=[CH:33][CH:32]=[CH:39][C:38]=4[OH:37])=[CH:24][CH:23]=[CH:22][C:20]=3[CH:21]=1)=[O:40])[CH2:7]22.42 ml of a 1 M boron tribromide solution in dichloromethane are added dropwise to a suspension, cooled to −20° C., of 200 mg (0:48 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-(2-methoxyphenyl)-1-benzofuran-2-carboxamide hydrochloride (Example 102) in 8 ml of dichloromethane. After 2 h, the reaction is stopped by adding diethyl ether. The mixture is stirred at room temperature for 30 min and, after addition of water, neutralized with 1N sodium hydroxide solution. After extraction with ethyl acetate, the organic phases are combined and dried over sodium sulphate. Concentration and drying under high vacuum result in 125.9 mg (71.7% of theory) of the title compound.
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