2-BROMO-6-NITROPYRIDINE

In a 20 ml microwave tube was dissolved the crude title compound from Step A above, 2- bromo-6-nitropyridine (0.05 g, 0.245 mmol) in A/, A/'-dimethyacetamide (5.10 mL). Sodium carbonate (0.408 ml, 0.816 mmol) was added and the resulting stirring solution was degassed for 5 minutes. Then [1 , 1 '-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane was added (0.017 g, 0.02 mmol) and the reaction mixture was heated to 1 10C for 22 hours. TLC monitoring showed completion of the reaction. The reaction mixture was diluted with dichloromethane, insolubles were filtered out through Celite, and the filtrate was washed with water three times to remove residual amounts of A/, A/'-dimethylacetamide. The organic layer was dried MgS04, filtered and concentrated. The residue was purified via Biotage I solera One employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford the Comparative Example C7 (F-7) Precursor_as pale yellow solid (0.0174 g, 16 %). (0265) 'H-NMR (400 MHz, DMSO-d6) delta = 9.43 (s, 1 H), 9.38 (s, 1 H), 8.81 (d, 1 H), 8.60 (dd, 1 H), 8.33 (d, 1 H), 8.28-8.24 (m, 2H), 8.18 (d, 1 H), 8.10 (t, 1 H), 7.61 (d, 7H), 7.47 (d, 4H), 7.42 (d, 1 H), 7.28 (tt, 18H), 6.58 (d, 1 H), 6.19 (d, 1 H) (0266) MS (ESI): m/z = 533.62 [M+Hf.In a 20 ml microwave tube was dissolved the crude title compound from Step A above, 2- bromo-6-nitropyridine (0.05 g, 0.245 mmol) in Lambda/, /V'-dimethylacetamide (5.10 mL). Sodium carbonate (0.408 ml, 0.816 mmol) was added and the resulting stirring solution was degassed for 5 minutes. Then [1, 1'-bis(diphenylphosphino)ferrocene]dichloropalladium(ll) complex with dichloromethane was added (0.017 g, 0.02 mmol) and the reaction mixture was heated to 110C for 22 hours. TLC monitoring showed completion of the reaction. The reaction mixture was diluted with dichloromethane, insolubles were filtered out through Celite, and the filtrate was washed with water three times to remove residual amounts of /V, /V-dimethylacetamide. The organic layer was dried MgS04, filtered and concentrated. The residue was purified via Biotage Isolera One employing an ethyl acetate/n-heptane gradient (5/95 -> 100/0 -> 100/0) to afford the Comparative Example C7 (F-7) Precursor as pale yellow solid (0.0174 g, 16 %). (0393) 1H-NMR (400 MHz, DMSO-d6) delta = 9.43 (s, 1 H), 9.38 (s, 1 H), 8.81 (d, 1 H), 8.60 (dd, 1 H), 8.33 (d, 1 H), 8.28-8.24 (m, 2H), 8.18 (d, 1 H), 8.10 (t, 1 H), 7.61 (d, 7H), 7.47 (d, 4H), 7.42 (d, 1H), 7.28 (tt, 18H), 6.58 (d, 1 H), 6.19 (d, 1 H) (0394) MS (ESI): m/z = 533.62 [M+H]+.The reaction vessel was charged with 2-phenylpyridine-5-boronic acid (3.36 g, 16.9 mmol), 2-bromo-6-methoxypyridine (3.43, Tetrakistriphenylphosphine palladium (0.7 g, 1.08 mmol), potassium carbonate (5.3 g, 38.3 mmol), toluene 500 mL, ethanol40mL and distilled water 40mL after stirring at 90 C for 3h. After completion of the reaction, the distilled water was quenched with ethyl acetate take. The organic layer is dried over MgSO4. The solvent was distilled off under reduced pressure and then purified on a silica gel column to give compound 3-5-A (1.64 g, 35%).Example 90A methyl (3S)-1-(6-nitropyridin-2-yl)pyrrolidine-3-carboxylate A mixture of (S)-methyl pyrrolidine-3-carboxylate, hydrochloric acid (204 mg, 1.232 mmol), Example 7A methyl (3R)-1-(6-nitropyridin-2-yl)pyrrolidine-3-carboxylate A mixture of (R)-methyl pyrrolidine-3-carboxylate, hydrochloric acid (204 mg, 1.232 mmol),

Molecular Weight:202.99
XLogP3:2
Hydrogen Bond Acceptor Count:3
Exact Mass:201.93779
Monoisotopic Mass:201.93779
Topological Polar Surface Area:58.7
Heavy Atom Count:10
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes