[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.Cl.Cl[C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.[OH2:19].[C:20](=[O:23])([O-:22])[O-].[Na+].[Na+].CN1C[CH2:30][CH2:29][C:28]1=[O:32]>>[C:28]([OH:32])(=[O:19])/[CH:29]=[CH:30]\[C:20]([OH:22])=[O:23].[N:16]1[CH:17]=[CH:18][C:13]([NH:1][C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[NH:4][CH:3]=2)=[CH:14][CH:15]=1A solution of 3-aminoindole (8 g) and 4-chloropyridine hydrochloride (12 g) in 150 mL 1-methyl-2-pyrrolidinone was stirred at 70°-75° C. for one hour, after which additional 4-chloropyridine hydrochloride (4 g) was added. After stirring a total of two hours, the mixture was cooled, stirred with water, basified with sodium carbonate and extracted with ethyl acetate. The organic extract was washed successively with water and a saturated sodium chloride solution and thereafter dried (anhydrous magnesium sulfate), filtered and concentrated to 20 g of a dark oil. This was eluted through silica with 20% methanol in dichloromethane via HPLC (high performance liquid chromatography) yield 7 g of dark oil. This oil was crystallized from acetonitrile to yield 3 g light brown crystals, m.p. 192°-193°. A 2.8 g portion was converted to the maleate salt in 50% methanol/ether to yield 3.5 g of light tan crystals, m.p. 149°-151° C. Recrystallization from 50% methanol/ether yielded 3.4 g of light tan crystals, m.p. 149°-151° C.
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