Patent ID: 8461342

Claim:
A process for preparing a compound of formula I: comprising the step of: ia) reacting a compound of formula 6a: wherein, R is H, C 1-6 aliphatic, aryl, aralkyl, heteroaryl, cycloalkyl, or heterocycloalkyl; R 1 is independently selected from —R J , —OR J , —N(R J ) 2 , —NO 2 , halogen, —CN, —C 1-4 haloalkyl, —C 1-4 haloalkoxy, —C(O)N(R J ) 2 , —NR J C(O)R J , —SOR J , —SO 2 R J , —SO 2 N(R J ) 2 , —NR J SO 2 R J , —COR J , —CO 2 R J , —NR J SO 2 N(R J ) 2 , —COCOR J ; R J is hydrogen or C 1-6 aliphatic; o is an integer from 0 to 3 inclusive; and p is an integer from 0 to 5 inclusive; with a compound of formula 7a: wherein, A is a fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl ring; R 1 is independently selected from —R J , —OR J , —N(R J ) 2 , —NO 2 , halogen, —CN, —C 1-4 haloalkyl, —C 1-4 haloalkoxy, —C(O)N(R J ) 2 , —NR J C(O)R J , —SOR J , —SO 2 R J , —SO 2 N(R J ) 2 , —NR J SO 2 R J , —COR J , —CO 2 R J , —NR J SO 2 N(R J ) 2 , —COCOR J ; R J is hydrogen or C 1-6 aliphatic; m is an integer from 0 to 3 inclusive; n is an integer from 1 to 4 inclusive; and X is a halo or OH; in an organic solvent in the presence of a second base, wherein compound 7a is prepared by the following steps ic) reducing Compound 10a in an organic solvent: wherein, A is a fused cycloalkyl, heterocycloalkyl, aryl, or heteroaryl ring; R 1 is independently selected from —R J , —OR J , —N(R J ) 2 , —NO 2 , halogen, —CN, —C 1-4 haloalkyl, —C 1-4 haloalkoxy, —C(O)N(R J ) 2 , —NR J C(O)R J , —SOR J , —SO 2 R J , —SO 2 N(R J ) 2 , —NR J SO 2 R J , —COR J , —CO 2 R J , —NR J SO 2 N(R J ) 2 , —COCOR J ; R J is hydrogen or C 1-6 aliphatic; R K is C 1-6 aliphatic; and m is an integer from 0 to 3 inclusive, with a reducing agent to produce Compound 11a: wherein, ring A, R 1 , and m are as defined in Compound 10a above; iic) reacting Compound 11a with a halogenating agent in an organic solvent to produce Compound 12a: wherein, ring A, R 1 , and m are as defined in Compound 10a above, and Hal is a halide; iiic) reacting Compound 12a with a cyanide to produce Compound 13a: wherein, ring A, R 1 , and m are as defined in Compound 10a above; ivc) reacting Compound 13a with a compound of formula 13aa in the presence of a base: wherein, Hal is a halide; and q is an integer from 0 to 3 inclusive; to produce a compound of formula 14a: wherein, r is an integer from 1 to 4 inclusive; and ring A, R 1 , and m are as defined in Compound 10a above; vc) sequentially reacting Compound 14a with a hydroxide base and acid to form Compound 15a, which is compound 7a when X=OH: wherein, r, ring A, R 1 , and m are as defined in Compound 14a above; and vic) reacting Compound 15a with a halogenating agent in an organic solvent to form Compound 16a, which is compound 7a when X=halide: wherein, Hal is halide; and r, ring A, R 1 , and m are as defined in Compound 14a above.