Patent ID: 8703979

Claim:
A process for preparing selectively one of a compound (Ia) and a compound (Ib) represented by following formula (Ia) and formula (Ib), respectively, over the other compound: wherein R 1 is selected from the group consisting of hydrogen; C 1-6 alkyl optionally substituted by hydroxy, C 1-6 alkoxy, or amino; C 5-10 aryl optionally substituted by hydroxy, C 1-6 alkoxy, or amino; 5- to 10-membered saturated or unsaturated heterocycle optionally substituted by hydroxy, C 1-6 alkoxy, or amino; CHO; CONH 2 ; C 1-6 alkylcarbonyl optionally substituted by hydroxy, C 1-6 alkoxy, or amino; and COC 5-10 aryl optionally substituted by hydroxy, C 1-6 alkoxy, or amino, and W is O or S, the method comprising: step (a) in which a compound (II) represented by following formula (II): wherein R 1 is defined above, is reacted in the presence of a base, a copper catalyst, and a palladium catalyst, in an aprotic polar solvent with a compound (III) represented by following formula (III): wherein R 2 is selected from the group consisting of hydrogen; C 1-6 alkyl optionally substituted by nitro, sulfo, cyano, acetyl, or C 5-10 aryl; COC 1-6 alkyl; and COC 5-10 aryl optionally substituted by nitro, sulfo, cyano, or acetyl, R 3 is selected from the group consisting of hydrogen; C 1-6 alkyl optionally substituted by nitro, sulfo, cyano, acetyl, or C 5-10 aryl; COC 1-6 alkyl; and COC 5-10 aryl optionally substituted by nitro, sulfo, cyano, or acetyl, and X is halogen selected from the group consisting of chlorine, bromine, and iodine; or OSO 2 CF 3 , wherein the compound (Ia) is formed selectively by including the palladium catalyst in an amount of less than a determining amount, and the compound (Ib) is formed selectively by including the palladium catalyst in an amount of no less than the determining amount.