[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1OS(C(F)(F)F)(=O)=O)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[F:38][C:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.C1(C)C=CC=CC=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7](=[O:24])[C:8]2[C:13]([C:14]=1[C:42]1[CH:43]=[CH:44][C:39]([F:38])=[CH:40][CH:41]=1)=[CH:12][C:11]([Cl:23])=[CH:10][CH:9]=2)=[O:4]A mixture of 2-benzyl-6-chloro-1-oxo-4-trifluoromethanesulfonyloxy-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (100 mg), sodium carbonate (45 mg), 4-fluorophenylboronic acid (35 mg), tetrakis(triphenylphosphine)palladium(0) (12 mg), toluene (2.0 ml), water (0.4 ml) and ethanol (0.4 ml) in a pear shape flask with dimroth was deaerated in a vacuum line, substituted with argon and stirred at 80° C. for 12 hrs. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative HPLC to give the title compound (52 mg) as a colorless powder.
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