[Br:1][C:2]1[C:3]([CH2:8][NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.O.C(=O)([O-])[O-].[K+].[K+]>O=P(Cl)(Cl)Cl>[Br:1][C:2]1[C:3]2[N:4]([C:10]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)=[N:9][CH:8]=2)[CH:5]=[CH:6][CH:7]=1A mixture of N-(3-bromopyridin-2-ylmethyl)-4-fluoro-benzamide (594 mg, 1.92 mmol) in POCl3 (5.0 mL) is warmed at reflux. After 1.5 hours, the mixture is cooled to room temperature and poured into water while adding crushed ice to control the exotherm. The mixture is made basic with potassium carbonate and the precipitate is collected by filtration to afford 8-bromo-3-(4-fluorophenyl)-imidazo[1,5-a]pyridine.
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