[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6].Br[C:23]1[N:28]=[CH:27][CH:26]=[CH:25][N:24]=1.C([O-])([O-])=O.[Na+].[Na+].O>C1COCC1.CC(P(C(C)(C)C)[C-]1C=CC=C1)(C)C.CC(P(C(C)(C)C)[C-]1C=CC=C1)(C)C.Cl[Pd]Cl.[Fe+2].CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]([C:23]2[N:28]=[CH:27][CH:26]=[CH:25][N:24]=2)[C:4]=1[C:5]([O:7][CH3:8])=[O:6]
In a microwave vial was dissolved methyl 2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (CAS 1146214-77-8) (500 mg, 1.71 mmol) and 2-bromopyrimidine (344 mg, 2.05 mmol) in THF (8.5 mL). Na2CO3 (544 mg, 5.14 mmol) was then added followed by water (4 mL) and the reaction mixture was degassed with N2 for 10 minutes. PdCl2(dtbpf) (CAS 95408-45-0) (45 mg, 0.069 mmol) was then added and the reaction mixture was heated at 80° C. for 4 h. The mixture was cooled to room temperature and water and EtOAc added. The reaction mixture was extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude was purified via silica gel chromatography (0-70% EtOAc in hexanes) to afford the title compound (265 mg, 63%). MS (ESI) mass calcd. for C13H12N2O3, 244.1. m/z found 245.1 [M+H]+. 1H NMR (400 MHz, Chloroform-d) δ 8.78 (d, J=4.9 Hz, 2H), 7.99 (dd, J=7.9, 0.9 Hz, 1H), 7.49 (t, J=8.1 Hz, 1H), 7.19 (t, J=4.8 Hz, 1H), 7.09 (dd, J=8.3, 0.9 Hz, 1H), 3.90 (s, 3H), 3.89 (s, 3H).
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