N[N:2]1[C:14]2[CH:13]=[N:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][C:5](Cl)=[CH:6][CH:7]=2.[F:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=1[F:26])[C:20](Cl)=O.[OH-:27].[Na+].[ClH:29].[N:30]1C=CC=CC=1>O>[Cl:29][C:6]1[CH:7]=[C:8]2[C:3](=[C:4]([NH:30][C:20](=[O:27])[C:19]3[CH:23]=[CH:24][C:25]([F:26])=[C:17]([F:16])[CH:18]=3)[CH:5]=1)[NH:2][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1
To a cold (3° C.–5° C.) solution of 9-amino-7-chloro-β-carboline (2.50 g, 11.5 mmol, as prepared in example 60 above) in pyridine (130 ml) was added 3,4-diflourobenzoyl chloride (1.67 ml, 13.25 mmol). The reaction was allowed to warm to RT and stirred for 20 h before diluting the reaction with water (60 ml) and 1M NaOH (15 ml). After stirring for 3 h at RT, the pH of the mixture was adjusted to 8–9 with 1M HCl and then poured into water (250 ml). The mixture was allowed to stand for 30 min and the product was filtered to provide 3.95 g of the title compound after washing with water and drying under reduced pressure at 55° C.–60° C.
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