Cl[C:2]1[CH:3]=[C:4]([CH:11]=[C:12]([O:14][CH3:15])[N:13]=1)[C:5]([NH:7][CH:8]1[CH2:10][CH2:9]1)=[O:6].[CH3:16][O:17][CH2:18]/[CH:19]=[CH:20]/B1OC(C)(C)C(C)(C)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.[Pd](Br)Br>[CH:8]1([NH:7][C:5](=[O:6])[C:4]2[CH:3]=[C:2](/[CH:20]=[CH:19]/[CH2:18][O:17][CH3:16])[N:13]=[C:12]([O:14][CH3:15])[CH:11]=2)[CH2:10][CH2:9]1
To a solution of 2-chloro-N-cyclopropyl-6-methoxyisonicotinamide from the previous step (1 eq.) in DMF (0.3 M) was added (2-[(1E)-3-methoxyprop-1-en-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 eq.), palladium bromide (5% loading), triphenylphosphine (10% loading) and sodium carbonate (2 M aqueous solution, 3 eq.). The resulting suspension was heated at 100° C. for 7 h. The reaction mixture was quenched with water and extracted with ether. The combined organic extracts were washed with sat. aq. NaHCO3 and brine. Drying over Na2SO4, filtration and concentration of the filtrate in vacuo afforded the crude product as a brown tar. Purification by way of column chromatography (SiO2, 1:1 (v/v) Hex:EtOAc) followed by recrystallization from Hex:ether afforded the title compound as a white solid.
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