Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1.[F:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH3:9])[CH:3]=1
4-Bromo-2-methoxypyridine (1.39 g, 7.42 mmol), 2-fluoro-4-methoxyphenylboronic acid (2.40 g, 14.1 mmol), K2CO3 (2.05 g, 14.8 mmol) and bis(triphenylphosphine) palladium(II) chloride (Pd(PPh3)2Cl2) (52 mg, 0.74 mmol) were stirred in DMSO (8.5 mL) under vacuum for 20 min. The flask was flushed with argon and the mixture was heated to 90° C. for 3 h. Upon cooling, the mixture was diluted with brine, and the aqueous solution was extracted with CH2Cl2 (3×50 mL). The combined organic extracts were washed with water (3×20 mL), dried over Na2SO4 and concentrated under reduced pressure. Flash chromatography (40+M Biotage column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 to 80:20) provided the title compound (0.98 g, 57%) as a yellow oil: 1H NMR (500 MHz, CDCl3) δ 8.20 (d, J=5.4 Hz, 1H), 7.42-7.38 (m, 1H), 7.07 (d, J=5.4 Hz, 1H), 6.93 (s, 1H), 6.80 (dd, J=8.6, 2.5 Hz, 1H), 6.74 (dd, J=12.6, 2.5 Hz, 1H), 3.99 (s, 3H), 3.85 (s, 3H).
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