[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[C:22](Br)=[CH:21][C:20]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:19][N:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1.[CH2:31](B(O)O)[CH3:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([O:16][C:17]2[C:22]([CH2:31][CH3:32])=[CH:21][C:20]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:19][N:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1A mixture of [4-(3-bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (42 mg, 0.085 mmol), ethylboronic acid (15 mg, 0.20 mmol), bis(triphenylphosphine)dichloropalladium(II) (7.0 mg, 0.01 mmol), potassium phosphate (64 mg, 0.30 mmol), triphenylphosphine (15.2 mg, 0.05 mmol) and toluene (1 mL) was stirred at 100° C. overnight under an argon atmosphere. The resulting mixture was filtered. The filtrate was concentrated in vacuo. The residue was purified by preparative TLC (20% ethyl acetate in petroleum ether) to afford [4-(5-ethanesulfonyl-3-ethyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (18 mg, 47.6%) as a white solid.
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