Cl[C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([Cl:15])[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH:16]([B-](F)(F)F)=[CH2:17].[K+].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C1COCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[Cl:15][C:13]1[CH:12]=[C:4]([CH:3]=[C:2]([CH:16]=[CH2:17])[N:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]To a solution of tert-butyl 2,6-dichloroisonicotinate (11.0 g, 44.3 mmol) in THF (200 mL) were added potassium vinyltrifluoroborate (7.1 g, 53.2 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.97 g, 1.33 mmol) and triethylamine (9.3 mL, 66.5 mmol). The mixture was heated to 65° C. After 1 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→90% hexanes/ethyl acetate) gave no separation of desired product. The mixture was carried onto next step.
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