Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25](I)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1B(O)O.[C:37]([O-])([O-])=[O:38].[K+].[K+]>[Pd].CCO.COCCOC>[Cl:2][C:3]1[CH:4]=[C:5]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:33]4[O:29][C:30]([CH:37]=[O:38])=[CH:31][CH:32]=4)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1A mixture of compound 8.3 (489 mg, 1.0 mmol), 2-furylboronic acid (185 mg, 1.2 mmol) and palladium catalyst (73.0 mg, 0.10 mmol) in 1.0 mL of K2CO3 (2.0M), 1.0 mL of EtOH and 4.0 mL of DME was heated at 75° C. under nitrogen atmosphere for 4 hr. LS-MS showed the reaction completed. Concentrated the mixture under reduced pressure and washed the residue with water (2×5.0 mL) then with cool ether (10.0 mL) to get a gray solid (400 mg), which was used for next step without further purification.
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