Method for producing biaryl compound

摘要

The invention provides a production method of a biaryl compound of the formula [3] or a salt thereof, including reacting a 2-phenylazole derivative of the formula [1] or a salt thereof, with a benzene derivative of the formula [2] or a salt thereof in the presence of a metal catalyst, a base, and one or more of (a) a monocarboxylic acid metal salt, (b) a dicarboxylic acid metal salt, (c) a sulfonic acid metal salt, and (d) a phosphate or phosphoric amide metal salt represented by RAxP(O)(OM)y;
wherein each symbol is as defined herein.

主权项

1. A method of producing a biaryltetrazole compound represented by the formula [3′]:wherein
R1 to R4 are each independently a hydrogen atom, or an alkyl group, an aralkyl group or an aryl group, each of which optionally has 1 to 5 substituents that are the same or different and that are selected from
(1) halogen atom;(2) hydroxy;(3) amino;(4) nitro;(5) cyano;(6) a heterocyclic group optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl, and mono- or di-C6-14 aryl-sulfamoyl;(7) mono- or di-C1-6 alkyl-amino;(8) mono- or di-C6-14 aryl-amino;(9) mono- or di-C7-14 aralkyl-amino;(10) N-C1-6 alkyl-N-C6-14 aryl-amino;(11) N-C1-6 alkyl-N-C7-14 aralkyl-amino;(12) C3-8 cycloalkyl;(13) optionally halogenated C1-6 alkoxy;(14) C1-6 alkylsulfanyl;(15) C1-6 alkylsulfinyl;(16) C1-6 alkylsulfonyl;(17) optionally esterified carboxy;(18) C1-6 alkyl-carbonyl;(19) C3-8 cycloalkyl-carbonyl;(20) C6-14 aryl-carbonyl;(21) carbamoyl;(22) thiocarbamoyl;(23) mono- or di-C1-6 alkyl-carbamoyl;(24) mono- or di-C6-14 aryl-carbamoyl;(25) N-C1-6 alkyl-N-C6-14 aryl-carbamoyl;(26) mono- or di-5- to 7-membered heterocyclyl-carbamoyl;(27) C1-6 alkyl-carbonylamino optionally substituted by carboxy;(28) C6-14 aryloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl and mono- or di-C6-14 aryl-sulfamoyl;(29) C6-14 aryl optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl and mono- or di-C6-14 aryl-sulfamoyl;(30) heterocyclyl-oxy;(31) sulfamoyl;(32) mono- or di-C1-6 alkyl-sulfamoyl;(33) mono- or di-C6-14 aryl-sulfamoyl;(34) C7-14 aralkyloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl and mono- or di-C6-14 aryl-sulfamoyl;(35) C1-6 alkyl-carbonyloxy;(36) C1-6 alkoxy-carbonyl; and(37) tri-C1-6 alkylsilyloxy; R5′ is a methyl group, a methyl group substituted by a protected hydroxyl group, or a lower alkoxycarbonyl group, and R6 is a tetrazolyl-protecting group, or a salt thereof, comprising reacting a 2-phenylazole derivative represented by the formula [1′]:wherein
R1 to R4 are each independently a hydrogen atom, or an alkyl group, an aralkyl group or an aryl group, each of which optionally has 1 to 5 substituents that are the same or different and that are selected from
(1) halogen atom;(2) hydroxy;(3) amino;(4) nitro;(5) cyano;(6) a heterocyclic group optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl, and mono- or di-C6-14 aryl-sulfamoyl;(7) mono- or di-C1-6 alkyl-amino;(8) mono- or di-C6-14 aryl-amino;(9) mono- or di-C7-14 aralkyl-amino;(10) N-C1-6 alkyl-N-C6-14 aryl-amino;(11) N-C1-6 alkyl-N-C7-14 aralkyl-amino;(12) C3-8 cycloalkyl;(13) optionally halogenated C1-6 alkoxy;(14) C1-6 alkylsulfanyl;(15) C1-6 alkylsulfinyl;(16) C1-6 alkylsulfonyl;(17) optionally esterified carboxy;(18) C1-6 alkyl-carbonyl;(19) C3-8 cycloalkyl-carbonyl;(20) C6-14 aryl-carbonyl;(21) carbamoyl;(22) thiocarbamoyl;(23) mono- or di-C1-6 alkyl-carbamoyl;(24) mono- or di-C6-14 aryl-carbamoyl;(25) N-C1-6 alkyl-N-C6-14 aryl-carbamoyl;(26) mono- or di-5- to 7-membered heterocyclyl-carbamoyl;(27) C1-6 alkyl-carbonylamino optionally substituted by carboxy;(28) C6-14 aryloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl and mono- or di-C6-14 aryl-sulfamoyl;(29) C6-14 aryl optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl and mono- or di-C6-14 aryl-sulfamoyl;(30) heterocyclyl-oxy;(31) sulfamoyl;(32) mono- or di-C1-6 alkyl-sulfamoyl;(33) mono- or di-C6-14 aryl-sulfamoyl;(34) C7-14 aralkyloxy optionally substituted by 1 to 3 substituents selected from halogen atom, hydroxy, amino, nitro, cyano, optionally halogenated C1-6 alkyl, mono- or di-C1-6 alkyl-amino, C6-14 aryl, mono- or di-C6-14 aryl-amino, C3-8 cycloalkyl, C1-6 alkoxy, C1-6 alkoxy-C1-6 alkoxy, C1-6 alkylsulfanyl, C1-6 alkylsulfinyl, C1-6 alkylsulfonyl, optionally esterified carboxy, carbamoyl, thiocarbamoyl, mono- or di-C1-6 alkyl-carbamoyl, mono- or di-C6-14 aryl-carbamoyl, sulfamoyl, mono- or di-C1-6 alkyl-sulfamoyl and mono- or di-C6-14 aryl-sulfamoyl;(35) C1-6 alkyl-carbonyloxy;(36) C1-6 alkoxy-carbonyl; and(37) tri-C1-6 alkylsilyloxy; and R6 is a tetrazolyl-protecting group,or a salt thereof with a benzene derivative represented by the formula [2′]:wherein R5′ is a methyl group, a methyl group substituted by a protected hydroxyl group, or a lower alkoxycarbonyl group, and X′ is a leaving group,
in the presence of a metal catalyst, a base and one or more kinds of compounds selected from the group consisting of the following (a)-(c); (a) a metal salt of glutarate, (b) a metal salt of 4-dodecylbenzenesulfonate, and (c) a metal salt of bis(2-ethylhexyl) phosphate.