Br[C:2]1[C:11]2[C:6]3=[C:7]([CH2:12][CH2:13][O:14][C:5]3=[CH:4][CH:3]=1)[CH:8]=[CH:9][N:10]=2.[B:15]1(B2OC(C)(C)C(C)(C)O2)[O:19]C(C)(C)C(C)(C)[O:16]1.C([O-])(=O)C.[K+]>O1CCOCC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Pd]>[O:14]1[C:5]2[C:6]3[C:11]([C:2]([B:15]([OH:19])[OH:16])=[CH:3][CH:4]=2)=[N:10][CH:9]=[CH:8][C:7]=3[CH2:12][CH2:13]17-bromo-2.3-dihydropyrano[4.3.2-de]quinoline (0.170 g; 0.680 mmol), bis(pinacolato)diboron (0.207 g; 0.816 mmol), anhydrous potassium acetate (0.133 g; 1.36 mmol) and bis(tricyclohexylphosphine)palladium(0) (0.045 g; 0.068 mmol) in anhydrous 1.4-dioxane (3.1 mL) were mixed in a tube, purged with argon and sealed. After heating at 95° C. for 16 h, the mixture was cooled at room temperature, concentrated under reduced pressure and store at 3° C. for 21 h. The brown residue was dissolved in acetonitrile, filtered, and the dark brown solution was concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 1) furnished 0.044 g (25%) of the title compound as an amorphous solid.
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