Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1.ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:2]2[N:7]=[CH:6][C:5]3[CH:8]=[N:9][NH:10][C:4]=3[CH:3]=2)[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1A mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (500 mg, 3.2 mmol) (Frontier Cat. No. Z13659), (3,5-dimethoxyphenyl)boronic acid (890 mg, 4.9 mmol) (TCI Cat. No. D3513), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (200 mg, 0.3 mmol), and sodium carbonate (1.0 g, 9.8 mmol) in 1,2-dimethoxyethane (4 mL) and water (0.6 mL) was degassed, and sealed. The mixture was stirred at 110° C. overnight. After cooling it was partitioned between ethyl acetate and water. After separation the aqueous solution was extracted with ethyl acetate twice. The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-50%) to afford the desired product (0.80 g). LCMS (M+H)+=256.0.
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