Pyridine → 1-(4-Fluorophenyl)-5-iodo-6-methylindazole

HRID 1098831Notes

Reaction equation

HRID 1098831 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[NH:7][N:6]=[CH:5]2.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([I:1])=[C:10]([CH3:11])[CH:9]=3)[CH:5]=[N:6]2)=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 2856454-Fluorophenylboronic acid2×HCID 593396965-iodo-6-methyl-1H-indazole

Product 1

HCID 593399141-(4-Fluorophenyl)-5-iodo-6-methylindazoleYield 51.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalyst2×HCID 6344DichloromethaneSolvent

Procedure

5-Iodo-6-methylindazole (1.3 g, 5.0 mmol), p-fluorobenzeneboronic acid (1.4 g, 10 mmol), anhydrous copper(II) acetate (1.4 g, 7.5 mmol) and pyridine (0.80 mL, 10 mmol) were stirred in dichloromethane (30 mL) overnight. Additional portions of p-fluorobenzeneboronic acid (0.47 g, 3.4 mmol), anhydrous copper(II) acetate (0.45 g, 2.5 mmol) and pyridine (0.27 mL, 3.4 mmol) were added. The mixture was filtered through celite after stirring for an additional night. The filtrate was concentrated and purified by column chromatography (SiO2, toluene) to give the subtitle compound (0.90 g, 51%) as a light orange powder.

Workup

  1. filtrationThe mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. custompurified by column chromatography (SiO2, toluene)

Sources & evidence

ORD record
ord-2ddaf770e336452fa64a04bd6a684a14
Source dataset
uspto-grants-2012_03
Patent number
US08143290B2

Reaction notes

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