Transition metal catalyzed synthesis of 2H-indazoles

1. A process for preparing a compound of formula I

and/or all stereoisomeric forms of the compound of formula I, and/or mixtures of these forms in any ratio, and/or a physiologically tolerated salt of the compound of formula I, wherein;

A1, A2, A3 and A4 form together with the two carbon atoms in formula I form a benzene,

Q is a covalent bond,

—(C 1 -C 6 )-alkylene,

—(C 3 -C 6 )-cycloalkyl,

phenyl, wherein phenyl is unsubstituted or mono-, di-, tri- or four times substituted independently of one another by R13;

—(C 1 -C 4 )-alkylene-O—(C 1 -C 4 )-alkylene,

—(C 1 -C 4 )-alkylene-O—; or

—(C 5 -C 14 )-heteroaryl is selected from pyridyl, quinolinyl, tetrahydropyranyl and thienyl,

J is a covalent bond, —(C 1 -C 6 )-alkylene, —(C 3 -C 6 )-cycloalkyl, phenyl, naphthyl, or —(C 5 -C 14 )-heteroaryl, wherein heteroaryl is as defined above,

R0, R1, R2, R3 and R4 are independent of one another identical or different and are a) hydrogen atom,

b) —(C 1 -C 4 )-alkyl, wherein alkyl is unsubstituted or substituted one, two or three times by R13,

c) F, Cl or Br,

d) naphthyl, wherein naphthyl is unsubstituted or substituted one, two or three times by R13,

e) phenyl, wherein phenyl is unsubstituted or substituted one, two or three times by R13,

f) —(C 5 -C 14 )-heteroaryl, wherein heteroaryl is as defined above,

g) —(C 3 -C 6 )-cycloalkyl,

h) —O—(C 1 -C 4 )-alkyl,

i) —CN,

j) —OH,

k) —C(O)—R10,

l) —C(O)—O—R11,

m) —C(O)—N(R11)-R12,

n) —N(R11)-R12, or

p) —O—SO 2 —R13,

R5 is a) —(C 1 -C 4 )-alkyl, wherein alkyl is unsubstituted or substituted one, two or three times by R13,

b) F, Cl or Br,

c) naphthyl, wherein naphthyl is unsubstituted or substituted one, two or three times by R13,

d) phenyl, wherein phenyl is unsubstituted or substituted one, two or three times by R13,

e) —(C 5 -C 14 )-heteroaryl, wherein heteroaryl is as defined above,

f) —(C 3 -C 6 )-cycloalkyl,

g) —O—(C 1 -C 4 )-alkyl,

h) —CN,

i) —OH,

j) —C(O)—R10,

k) —C(O)—R11,

l) —C(O)—N(R11)-R12,

m) —N(R11)-R12, or

n) —O—SO 2 —R13,

R10 is hydrogen atom or —(C 1 -C 4 )-alkyl,

R11 and R12 are independently of one another identical or different and are hydrogen atom or —(C 1 -C 4 )-alkyl, wherein alkyl is unsubstituted or mono-, di- or trisubstituted independently of one another by R13,

R13 is F, Cl, —CN, —OH, —(C 1 -C 4 )-alkoxy, —CF 3 or phenyl, wherein phenyl is unsubstituted or mono-, di- or trisubstituted independently of one another by R14,

R14 is F, Cl, —OH, —CN, —CF 3 , —(C 1 -C 4 )-alkyl or —(C 1 -C 4 )-alkoxy, said process comprises reacting a compound of formula II

wherein R0, R1, R2, R3, R4, A1, A2, A3, A4 and Q are as defined in formula I and X is Cl, Br, I or tosylate,

with a compound of formula III or any salts thereof,

wherein J and R5 are as defined in formula I,

in the presence of a transition metal catalyst selected from the group Pd-halides, Pd-halide complexes, Pd-phosphine complexes and Pd-alkene complexes to give a compound of formula I and

optionally the compound of formula I is converted to its physiologically tolerated salt; wherein the compounds of formula I prepared are selected from the group consisting of: 3-Benzyl-2-phenyl-2H-indazole; 2-Phenyl-3-pyridin-2-ylmethyl-2H-indazole; 2-Phenyl-3-(4-trifluoromethyl-benzyl)-2H-indazole; 2-Phenyl-3-(4-methoxy-benzyl)-2H-indazole; 3-(6-Methoxy-naphthalen-2-ylmethyl)-2-phenyl-2H-indazole; N,N-Diisopropyl-2-(2-phenyl-2H-indazol-3-yl)-acetamide; (2-Phenyl-2H-indazol-3-yl)-acetic acid tert-butyl ester; 3-(2,2-Diethoxy-ethyl)-2-phenyl-2H-indazole; 3-(2,2-Dimethyl-propyl)-2-phenyl-2H-indazole; 3-Hexyl-2-phenyl-2H-indazole; 3-Cyclopropylmethyl-2-phenyl-2H-indazole-6-carboxylic acid tert-butyl ester; 3-Benzyl-2-phenyl-2H-indazole-6-carboxylic acid tert-butyl ester; 3-Cyclopentylmethyl-2-phenyl-2H-indazole-6-carboxylic acid tert-butyl ester; Diethyl-[2-(2-phenyl-2H-indazol-3-yl)-ethyl]-amine; 2-Phenyl-3-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-2H-indazole; 3-Benzyl-2-phenyl-5-trifluoromethyl-2H-indazole; 3-Benzyl-6-fluoro-2-phenyl-2H-indazole; 3-Benzyl-4-methyl-2-phenyl-2H-indazole; 3-Benzyl-6-methoxy-2-phenyl-2H-indazole; 3-Benzyl-5-methoxy-2-phenyl-2H-indazole; Toluene-4-sulfonic acid 3-benzyl-2-phenyl-2H-indazol-6-yl ester; 3-Benzyl-2-phenyl-2H-indazole-5-carboxylic acid; 3-Benzyl-2-phenyl-2H-pyrazolo[4,3-c]pyridine; 3-Benzyl-2-(4-methoxy-phenyl)-2H-indazole; 3-Benzyl-2-(4-fluoro-phenyl)-2H-indazole; 3-Benzyl-2-(2-fluoro-phenyl)-2H-indazole; 4-(3-Benzyl-indazol-2-yl)-benzonitrile; 3-Benzyl-2-naphthalen-1-yl-2H-indazole; 3-Benzyl-2-pyridin-4-yl-2H-indazole; 4-(3-Benzyl-indazol-2-yl)-quinoline; 3-Benzyl-2-pyridin-4-yl-2H-indazole-6-carboxylic acid tert-butyl ester; 3-Cyclopropylmethyl-2-pyridin-4-yl-2H-indazole-6-carboxylic acid tert-butyl ester; 3-Benzyl-2-methyl-2H-indazole; 3-Benzyl-2-phenethyl-2H-indazole; 3-Benzyl-2-isopropyl-2H-indazole; 3-Benzyl-2-cyclohexyl-2H-indazole and 3-Benzyl-2-thiophen-2-ylmethyl-2H-indazole-6-carboxylic acid tert-butyl ester.