Patent ID: 8222425

Claim:
A method of making a compound of Formula V: the method comprising the steps of (a) providing a compound of Formula III: (b) providing a compound of Formula IV: (c) contacting the compound of Formula III with the compound of Formula IV and a base in a solvent under conditions conducive to formation of a compound of Formula II: (d) contacting the compound of Formula II with an inorganic or organometallic compound or salt comprising at least one metal hydrogen bond in a solvent under conditions conducive to formation of a compound of Formula VI: (e) contacting the compound of Formula VI with dihydrogen and a hydrogenation catalyst in a solvent under conditions conducive to formation of a compound of Formula V: wherein x is zero, one or two; Z 1 and Z 3 are each independently selected CR 8 R 9 ; Z 2 is absent or is selected from the group consisting of O, S, CR 8 R 9 , or NR 10 ; R 6 , R 7 , R 13 and R 14 are independently selected from the group consisting of hydrogen, C 1-6 alkyl, or aryl; or R 6 and R 7 taken in combination form a three to six membered saturated three to seven membered carbocycle, which is optionally substituted by zero to three substituents; R 8 , R 9 , R 11 and R 12 are independently selected from the group consisting of hydrogen, halogen, C 1-6 alkyl, C 1-6 alkoxy, haloC 1-6 alkyl, haloC 1-6 alkoxy, hydroxyC 1-6 alkyl, C 1-6 alkoxyC 1-6 alkyl, or aryl; or R 11 and R 12 taken in combination form a three to six membered saturated three to seven membered carbocycle, which is optionally substituted by zero to three substituents; R 10 is selected from hydrogen, C 1-6 alkyl, haloC 1-6 alkyl, hydroxyC 1-6 alkyl, C 1-6 alkoxyC 1-6 alkyl, aryl and aralkyl; R 15 is hydrogen, C 1-10 alkyl, C 3-10 cycloalkyl, aryl, or heteroaryl; R 16 is C 1-10 alkyl, C 3-10 cycloalkyl, aryl, or heteroaryl; and R 17 is cyano, nitro, C 1-6 alkylsulfonate, haloC 1-6 alkylsulfonate, arylsulfonate, or halogen.