Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15](B(O)O)=[CH:14][C:13]=1[CH3:21].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15]([C:2]2[C:3]([CH3:9])=[CH:4][CH:5]=[C:6]([NH2:8])[N:7]=2)=[CH:14][C:13]=1[CH3:21]
6-Chloro-5-methylpyridin-2-amine (1.426 g, 10 mmol), 6-methoxy-5-methylpyridin-3-ylboronic acid (2.0 g, 12 mmol) and Pd(PPh3)4 (577.8 mg, 0.5 mmol) were combined in a flask. DME (100 mL) was added followed by aqueous Na2CO3 (10.00 mL of 2 M, 20.0 mmol). The flask was fitted with a condenser and heated at 80° C. for 12 hours under N2 atmosphere. More Pd(PPh3)4 (577.8 mg, 0.5 mmol) was added, the condenser was removed and the flask was fitted with a rubber stopper. N2 (g) was flushed through the flask and the reaction was stirred at 80° C. for an additional 12 hours under N2(g) balloon. The reaction mixture was filtered through a bed of Celite, the Celite was washed with ethyl acetate and the combined filtrates were concentrated. The residue was purified by column chromatography (30-100% ethyl acetate-Hexanes) to yield 680 mg of the product as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 8.10 (s, 1H), 7.66 (s, 1H), 7.29 (d, J=8.3 Hz, 1H), 6.37 (d, J=8.3 Hz, 1H), 5.75 (s, 2H), 3.91 (s, 3H), 2.18 (s, 3H), 2.14 (s, 3H). ESI-MS m/z calc. 229.1. found 230.5 (M+1)+. Retention time 0.91 minutes.
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