Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[NH:8][CH2:7][CH2:6][CH2:5]2.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:2]2[CH:3]=[C:4]3[C:9](=[N:10][CH:11]=2)[NH:8][CH2:7][CH2:6][CH2:5]3)[CH:13]=16-Bromo-1,2,3,4-tetrahydro-[1,8]naphthyridine (243 mg, 1.1 mmol), 3-pyridinyl-boronic acid (168 mg, 1.4 mmol) and K2CO3 (315 mg, 2.3 mmol) are mixed in 3.0 mL of 1,4-dioxane and 0.30 mL of water. Argon gas is bubbled through the mixture for 10 min and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (81 mg, 0.11 mmol) is added. The mixture is heated at 100° C. for 16 hrs. Then solvents are removed and EtOAc (50 mL) is added along with 30 mL of water. The mixture is filtered to remove any solid and the organic layer is separated. The aqueous layer is extracted with EtOAc (2×25 mL) and the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 143 mg of 6-Pyridin-3-yl-1,2,3,4-tetrahydro-[1,8]naphthyridine
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