| 主权项 |
1. A method of preparing a diol compound represented by the following Structural Formula:comprising the step of reacting a vinyl indazole compound represented by the following Structural Formula:with a dihydroxylation reagent, wherein:
each Rb independently is —H, halogen, —C(O)OR1, —C(O)R1, —C(S)R1, —OC(O)R1—, —C(O)NR1R2, —C(S)NR1R2, —OC(O)NR1R2, —S(O)R1, —S(O)2R1, —SO3R1, —SO2NR1R2, —OR1, —SR1, —NR1R2, —NR2C(O)R1, —NR2S(O)R1, —NR2C(O)OR1, —NR2C(O)ONR1R2, —N(R2)C(O)NR1R2, —NR2SO2NR1R2, —NR2SO2R1; —NO2, —CN, —NCS; or two ortho Ra groups taken together form —O—[CH2]p—O—, —S—[CH2]p—S— or —[CH2]q—; or C1-10 aliphatic group optionally substituted with one or more substituents selected from the group consisting halogen, nitro, cyano, —N(R21)2, —C(O)N(R21)2, —C(O)N(R21)2, —NR21C(O)R21, —SO2R22, —SO2N(R21)2, —NR21SO2R22, —NR21C(O)OR21, —OC(O)N(R21)2, —NR21C(O)N(R21)2, —NR21C(O)ON(R21)2, —NR21SO2N(R21)2, —OR21, —SR21, C1-10 haloalkoxy, —C(O)R21, —C(O)OR21 and —OC(O)R21; or (C0-10 alkylene)-Ar1, wherein Ar1 is a C6-14 aryl group or a 5-14 membered heteroaryl group, each optionally and independently substituted with one or more substituents selected from the group consisting of halogen, nitro, cyano, C1-10 alkyl, C1-10haloalkyl, (C1-10 haloalkoxy)C1-10 alkyl, (C1-10 alkoxy)C1-10 alkyl, C1-10 hydroxyalkyl, C1-10 aminoalkyl, (C1-10 alkylamino)C1-10 alkyl, (C1-10 dialkylamino)C1-10 alkyl, —N(R21)2, —C(O)N(R21)2, —C(O)N(R21)2, —NR21C(O)R21, —SO2R22, —SO2N(R21)2, —NR21SO2R22, NR21C(O)N(R21)2, —NR21C(O)ON(R21)2, —NR21SO2N(R21)2, —OR21, —SR21, C1-10 haloalkoxy, —C(O)R21, —C(O)OR21, —OC(O)R21, phenyl and 5-6 membered heteroaryl, wherein said phenyl and said 5-6 membered heteroaryl are each independently and optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, amino, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy and C1-3 haloalkoxy; each R1 independently is: i) hydrogen; ii) a C6-14 aryl group or a 5-14 membered heteroaryl group, each optionally and independently substituted with one or more substituents selected from the group consisting of halogen, —NO2, —CN, —NCS, C1-C10 aliphatic, (C1-10 alkylene)-Ar10, —C(O)OR10, —C(O)R10, —C(S)R10, —OC(O)R10, —C(O)N(R11)2, —C(S)N(R11)2, —OC(O)N(R11)2, —S(O)R12, —S(O)2R12, —SO3R12, —SO2N(R11)2, —OR10, —SR10, —N(R11)2, —NR11C(O)R10, —NR11S(O)R12, —NR11C(O)OR12, —N(R11)C(O)N(R11)2, —NR11SO2N(R11)2 and —NR11SO2R12; or iii) a C1-10 aliphatic group optionally substituted with one or more substituents selected from the group consisting of halogen, —NO2, —CN, —NCS, Ar10, —C(O)OR10, —C(O)R10, —C(S)R10, —OC(O)R10, —C(O)N(R11)2, —C(S)N(R11)2, —OC(O)N(R11)2, —S(O)R12, —S(O)2R12, —SO3R12, —SO2N(R11)2, —OR10, —SR10, —N(R11)2, —NR11C(O)R10, —NR11S(O)R12,—NR11C(O)OR12, —N(R11)C(O)N(R11)2, —NR11SO2N(R11)2 and —NR11SO2R12,
provided that R1 is other than hydrogen when Ra or Rb is —S(O)R1, —S(O)2R1, —SO3R1, —NR2S(O)R1 or —NR2SO2R1; and each R2 independently is —H or C1-C6 alkyl, or, taken together with NR1, forms a non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of ═O, ═S, halogen, nitro, cyano, hydroxy, C1-6 alkyl, C1-6 haloalkyl, C1-6 hydroxyalkyl, amino, C1-6 alkylamino, C1-6 dialkylamino, C1-6 aminoalkyl, (C1-6 alkylamino)C1-6 alkyl, (C1-6 dialkylamino)C1-6 alkyl, (phenyl)C1-6 alkyl, (5-6 membered heteroaryl)C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylcarbonyloxy, C1-6 alkoxycarbonyl, C1-6 alkylcarbonyl, phenyl and 5-6 membered heteroaryl; R3 is —H, halogen, C1-6 alkyl or C1-6 haloalkyl; each R10 independently is: i) hydrogen; ii) a C6-14 aryl group or a 5-14 membered heteroaryl group, each optionally and independently substituted with one or more substituents selected from the group consisting of halogen, nitro, cyano, hydroxy, C1-10 alkyl, C1-10 haloalkyl, (C1-10 haloalkoxy)C1-10 alkyl, (C1-10 alkoxy)C1-10 alkyl, C1-10 hydroxyalkyl, C1-10 aminoalkyl, (C1-10 alkylamino)C1-10 alkyl, (C1-10 dialkylamino)C1-10-alkyl, (phenyl)C1-10 alkyl, (5-6 membered heteroaryl)C1-10 alkyl, amino, C1-10 alkylamino, C1-10 dialkylamino, C1-10 alkoxy, C1-10 haloalkoxy, C1-10 alkylcarbonyloxy, C1-10 alkoxycarbonyl and C1-10 alkylcarbonyl; or iii) a C1-10 alkyl group optionally substituted with one or more substituents selected from the group consisting of halogen, nitro, cyano, hydroxy, C1-10 haloalkyl, C1-10 alkoxy, C1-10 haloalkoxy, amino, C1-10 alkylamino, C1-10 dialkylamino, C1-10 alkylcarbonyloxy, C1-10 alkoxycarbonyl, C1-10 alkylcarbonyl and phenyl, said phenyl being optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, amino, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy and C1-3 haloalkoxy; each R11 independently is R10, —CO2R10, —SO2R10 or —C(O)R10, or —N(R11)2 taken together is a non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of ═O, ═S, halogen, nitro, cyano, hydroxy, C1-6 alkyl, C1-6 haloalkyl, C1-6 hydroxyalkyl, amino, C1-6 alkylamino, C1-6 dialkylamino, C1-6 aminoalkyl, (C1-6 alkylamino)C1-6 alkyl, (C1-6 dialkylamino)C1-6 alkyl, C1-6 alkoxy, C1-6 haloalkoxy, C1-6 alkylcarbonyloxy, C1-6 alkoxycarbonyl and C1-6 alkylcarbonyl; and each R12 is independently is R10 provided that R12 is not hydrogen; each R21 independently is hydrogen, C1-6 alkyl, phenyl or 5-6 membered heteroaryl, wherein each of the phenyl and heteroaryl groups represented by R21 is independently and optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, amino, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy and C1-3 haloalkoxy, and wherein the alkyl group represented by R21 is optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, amino, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy and C1-3 haloalkoxy, and wherein the alkyl group represented by R21 is optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, amino, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy and C1-3 haloalkoxy; or N(R21)2 forms a non-aromatic heterocyclic group optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, ═O, C1-3 alky, C1-3 haloalkyl, C1-3 alkoxy, C1-3 haloalkoxy and amino; and each R22 independently C1-6 alkyl, phenyl or 5-6 membered heteroaryl, wherein each of the phenyl and heteroaryl groups represented by R22 is independently and optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, amino, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy and C1-3 haloalkoxy, and wherein the alkyl group represented by R22 is optionally substituted with one or more substituents selected from the group consisting of halogen, hydroxy, nitro, cyano, amino, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy and C1-3 haloalkoxy; each Ar10 independently is a C6-14 aryl group or a 5-14 membered heteroaryl group, each optionally and independently substituted with one or more substituents selected from the group consisting of halogen, nitro, cyano, —OH, —SH, —O(C1-10 alkyl), —S(C1-10 alkyl), C1-10 alkyl, C1-10 haloalkyl, (C1-10 haloalkoxy)C1-10 alkyl, (C1-10 alkoxy)C1-10 alkyl, C1-10 hydroxyalkyl, (C1-10 aminoalkyl, (C1-10 alkylamino)C1-10 alkyl, (C1-10 dialkylamino)C1-10 alkyl, (phenyl)C1-10 alkyl, (5-6 membered heteroaryl)C1-10 alkyl, amino, C1-10 alkylamino, C1-10 dialkylamino, C1-10 haloalkoxy, C1-10 alkylcarbonyloxy, C1-10 alkoxycarbonyl and C1-10 alkylcarbonyl; P1 is —H or a nitrogen protecting group; each p is 1, 2 or 3; each q is 2, 3, 4 or 5; and m is 1 or 2. |
