Preparation of N-aryl pyridones

A process for preparing a compound of formula V:

• comprising:
• (b) contacting a compound of formula IV with a compound of formula III in the presence of a metal salt and a second solvent;
• wherein:
• metal salt is selected from a copper and a palladium salt;
• the second solvent is an alcoholic or an aprotic solvent;
• R1 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R2 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R3 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R4 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R5 is selected from C1-20 alkyl, phenyl, and benzyl;
• R6 is selected from C1-8 alkyl, phenyl, and benzyl;
• R7 is selected from C1-18 alkyl, phenyl, and benzyl;
• R8 is selected from C1-18 alkyl, phenyl, and benzyl;
• L is a leaving group;
• Ar is an optionally substituted 5-10 membered aromatic carbocycle or heterocycle consisting of:
• carbon atoms and 04 heteroatoms selected from O, N, and S(O)p;
• and
• p is selected from 0, 1, and 2.

A compound of formula III:

• wherein:
• R1 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R2 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R3 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R4 is selected from H, C1-6 alkyl, OC1-6 alkyl, CF3, N(C1-6 alkyl)2, Cl, F, Br, I, phenyl, benzyl, —CN, and NO2;
• R5 is selected from C1-20 alkyl, phenyl, and benzyl;
• R6 is selected from C1-18 alkyl, phenyl, and benzyl;
• R7 is selected from C1-18 alkyl, phenyl, and benzyl;
• and
• R8 is selected from C-1-18 alkyl, phenyl, and benzyl.

A compound of formula Va:

• wherein:
• R1 is selected from H, C1-4 alkyl, Cl, F, and benzyl;
• R2 is selected from H, C1-4 alkyl, Cl, F, and benzyl;
• R3 is selected from H, C1-4 alkyl, Cl, F, and benzyl;
• R4 is selected from H, C1-4 alkyl, Cl, F, phenyl, and benzyl;
• R9 is selected from H, C1-6 alkyl, Cl, and F;
• R10 is selected from H, C1-6 alkyl, phenyl, benzyl, C1-6 alkyl-OH, O—C1-6 alkyl, C(O)—C1I6 alkyl, CO2—C1-16 alkyl, C(O)NH2, C(O)NH(C1-4 alkyl), C(O)N(C1-4 alkyl)2, NHC(O)C1-4 alkyl, N(C1-4 alkyl)C(O)C1-4 alkyl, S(O)p—C1-6 alkyl, S(O)pNH2, S(O)pNH(C1-4 alkyl), S(O)pN(C1-4 alkyl)2, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, C1-4 alkylene-NH2, C1-4 alkylene-NH(C1-4 alkyl), C1-4 alkylene-N(C1-4 alkyl)2, and NO2;
• R11 is selected from H, C1-6 alkyl, phenyl, benzyl, C1-6 alkyl-OH, O—C1-6 alkyl, C(O)—C1-6 alkyl, CO2—C1-6 alkyl, C(O)NH2, C(O)NH(C1-4 alkyl), C(O)N(C1-4 alkyl)2, NHC(O)C1-4 alkyl, N(C1-4alkyl)C(O)C1-4 alkyl, S(O)p—C1-6 alkyl, S(O)pNH2, S(O)pNH(C1-4 alkyl), S(O)pN(C1-4 alkyl)2, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, C1-4 alkylene-NH2, C1-4 alkylene-NH(C1-4 alkyl), C1-4 alkylene-N(C1-4 alkyl)2, and NO2;
• R12 is selected from H, C1-6 alkyl, phenyl, benzyl, C1-6 alkyl-OH, O—C1-6 alkyl, C(O)—C1-6 alkyl, CO2—C1-6 alkyl, C(O)NH2, C(O)NH(C1-4 alkyl), C(O)N(C1-4 alkyl)2, NHC(O)C1-4 alkyl, N(C1-4 alkyl)C(O)C1-4 alkyl, S(O)p—C1-6 alkyl, S(O)pNH2, S(O)pNH(C1-4 alkyl), S(O)pN(C1-4 alkyl)2, NH2, NH(C1-4 alkyl), N(C1-4 alkyl)2, C1-4 alkylene-NH2, C1-4 alkylene-NH(C1-4 alkyl), C1-4 alkylene-N(C1-4 alkyl)2, and NO2;
• R13 is selected from H, C1-6 alkyl, Cl, and F;
• and
• p, at each occurrence, is selected from 0, 1, and 2.