Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.CN([CH:23]=[O:24])C.[CH3:25][OH:26]>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]>[CH3:25][O:26][C:23]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2)=[O:24]To a mixture of 6-bromo-2H-isoquinolin-1-one (4.00 g, 17.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (750 mg, 0.92 mmol), triethylamine (9.0 mL, 65 mmol) in a Parr bomb add a 1:1 mixture (v/v) of DMF and MeOH. Seal the apparatus and flush with 100 psi of carbon monoxide (3×). Heat the reaction mixture at 70° C. with stifling for 15 h. Remove the solvent in vacuo and wash the residue with MeOH then crystallize from dichloromethane to give 3.11 g of the desired product 1-oxo-1,2-dihydro-isoquinoline-6-carboxylic acid methyl ester as an off white solid in 86% yield.
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