[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:15]([O-])=O)[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([F:18])[C:5]2=1.C([O-])=O.[NH4+].C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(O)C.CO>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([NH2:15])[CH:14]=1)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[C:6]([F:18])[C:5]2=1Sulfated platinum (0.1 eq, 1 g) was added to a suspension of 6-chloro-4-fluoro-8-nitro-9H-β-carboline (1.0 eq, 35 mmol, 9.3 g) and ammonium formate (3.0 eq, 105 mmol, 6.6 g) in ethanol (175 mL) and the resulting mixture heated at 75° C. for 4 h. After cooling to RT the mixture was filtered through a short plug of Celite® washing with copious amounts of methanol, and then the filtrate concentrated in vacuo to afford a beige solid. The solid was suspended in the minimum volume of methanol and added dropwise to a vigorously stirred mixture of saturated sodium bicarbonate solution and saturated sodium chloride solution. After stirring for 15 min the precipitated solids were collected by suction filtration, washed with water (200 mL) and dried in vacuo to afford 6-chloro-4-fluoro-9H-β-carbolin-8-ylamine (5.8 g, 70% 2 steps) as a beige powder. 1H-NMR (300 MHz, dmso-d6): δ 5.76 (s, 2H), 6.81 (d, 1H), 7.29 (d, 1H), 8.24 (d, 1H), 8.82 (d, 1H), and 11.71 (s, 1H). Retention Time (LC, method: ammonium acetate standard): 1.59 min. MS (M+H+): 236.
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