(2,5-Difluorophenyl)boronic acid → HCID 57516652, compound

HRID 1898634Notes

Reaction equation

HRID 1898634 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1B(O)O.[I:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1>[Cu]Cl.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N:16]1[CH:17]=[C:13]([I:12])[N:14]=[CH:15]1

Participants

5

Reactant 2

HCID 2734335(2,5-Difluorophenyl)boronic acidHCID 178506559HCID 178506559, compound

Product 1

HCID 57516652HCID 57516652, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 887MethanolSolvent

Procedure

Following a procedure similar to that outlined in Chem. Comm. 2004, 188-189: A solution of 2,5-difluorophenylboronic acid (47 mg, 0.30 mmol), 4-iodo-1H-imidazole (46 mg, 0.24 mmol), copper(I) chloride (1.8 mg, 0.018 mmol), and 1 mL of methanol was stirred under air at 60° C. for 3 h, then concentrated. Column chromatography (0-33% EtOAc/hexanes) afforded 14.5 mg (20%) of 1-(2,5-difluorophenyl)-4-iodo-1H-imidazole as a white solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-88a0c39b05d34cfc92505044f0d52ff0
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…