Patent ID: 7595338

Claim:
A method for preparing oxindole compounds comprising the steps of: (a) substituting a fluoroarene of formula I with a secondary nitrile in the presence of sodium hexamethyldisilazide or an isopropyl magnesium halide at about −40 to about 0° C.: wherein: X is halogen; R 1 , R 2 , and R 3 are, independently, selected from the group consisting of H, halogen, CN, C 1 to C 6 alkyl, substituted C 1 to C 6 alkyl, C 2 to C 6 alkenyl, substituted C 2 to C 6 alkenyl, C 2 to C 6 alkynyl, substituted C 2 to C 6 alkynyl, C 3 to C 8 cycloalkyl, substituted C 3 to C 8 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, N 2 + , OSO 2 CF 3 , CF 3 , NO 2 , SR 5 , OR 5 , N(R 5 ) 2 , COOR 5 , CON(R 5 ) 2 , and SO 2 N(R 5 ) 2 ; or R 1 and R 2 ; R 2 and R 3 ; or R 1 , R 2 , and R 3 are fused to form: (i) a 3 to 15 membered saturated or unsaturated carbon-containing ring; or (ii) a 3 to 15 membered heterocyclic ring containing in its backbone from 1 to 3 heteroatoms selected from the group consisting of O, S, and NR 11 ; wherein (i) or (ii) are optionally substituted by C 1 to C 6 alkyl, substituted C 1 to C 6 alkyl, halogen, C 1 to C 6 alkoxy, substituted C 1 to C 6 alkoxy, or N(R 5 ) 2 ; R 4 is fluorine; R 5 is selected from the group consisting of C 1 to C 6 alkyl and C 1 to C 6 substituted alkyl; G is C; A, D, and E are, independently, selected from the group consisting of C and N, wherein if any one of A, D, E, or G are N, the corresponding R 1 -R 3 is optionally absent; R 11 is absent, H, C 1 to C 6 alkyl, substituted C 1 to C 6 alkyl, aryl, or substituted aryl; or a pharmaceutically acceptable salt thereof; (b) converting the nitrile substituent of the product of step (a) to an amide; and (c) cyclizing the product of step (b) to said oxindole.