Cl[C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:12][CH3:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br-].[S:15]1[CH:19]=[CH:18][N:17]=[C:16]1[Zn+].N#N>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].C(Cl)Cl>[CH3:13][O:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([C:16]1[S:15][CH:19]=[CH:18][N:17]=1)[N:11]=[CH:10]22-Chloro-8-methoxyquinazoline (1.0 eq), and thiazol-2-ylzinc(II) bromide (1M in THF, 3 eq) was degassed by anhydrous N2 stream for 5 min followed by the addition of Pd(dppf)Cl2-DCM (0.1 eq). The reaction mixture was stirred at 50° C. for 1 hour. Solvents were removed under reduced pressure. The crude product was purified by column (10% methanol in ethyl acetate:hexanes=1:1) to give 2-(8-methoxyquinazolin-2-yl)thiazole (20%). LC/MS (m/z): 243.9 (MH+), Rt=0.68.
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