[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([O:22]C)[CH:21]=1)[C:5]([N:7]([CH:16]([CH3:18])[CH3:17])[CH2:8][CH2:9][C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)=[O:6].B(Br)(Br)Br.CO>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([OH:22])[CH:21]=1)[C:5]([N:7]([CH:16]([CH3:17])[CH3:18])[CH2:8][CH2:9][C:10]1[N:14]([CH3:15])[N:13]=[N:12][N:11]=1)=[O:6]To a stirred solution of 3-chloro-N-isopropyl-5-methoxy-N-[2-(1-methyl-1H-tetrazol-5-yl)-ethyl]-benzamide (0.115 g) in anhydrous dichloromethane (5.0 ml) at −78° C. was added 1M boron tribromide solution in dichloromethane (1.36 ml). The reaction mixture was stirred at this temperature for 15 min. The reaction was allowed to warm to room temperature. After 24 h, the reaction was cooled to −78° C. and methanol (1 ml) added. The reaction was allowed to rewarm to room temperature and absorbed on to silica. This was loaded on to an already prepared flash column, eluting with ethyl acetate:petroleum ether (4:1 v/v) and 25:1 dichloromethane:methanol (25:1 v/v) to give the title compound as a white solid (0.072 g).
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