Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=1.[CH3:19][C:20]1[N:21]=[C:22]([Sn](CCCC)(CCCC)CCCC)[S:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([C:10]2[S:11][CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=2)[N:3]=[C:2]([C:22]2[S:23][CH:24]=[C:20]([CH3:19])[N:21]=2)[CH:7]=1To a solution of compound 21 (4.17 mmol) in DMF (15 mL) were added 4-methyl-2-(tributylstannyl)thiazole (5 mmol), dichlorobis(triphenylphosphine) palladium (II) chloride (0.417 mmol), and K2CO3 (5 mmol). The reaction mixture was stirred at 110° C. under microwave irradiations for 1 hr. The solution was concentrated in vacuo and H2O and DCM were added. The layers were separated and the organic layer was concentrated. The crude was purified by silica gel chromatography (eluent: DCM) to give compound 22 in quantitative yield. MS (ESI, EI+): m/z=357.87 (MH+).
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