8-Hydroxyquinoline → (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol

HRID 1802626Notes

Reaction equation

[I:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[F:9].Cl.[OH:11][CH2:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[F:9][C:3]1[CH:4]=[C:5]([N:16]2[CH:17]=[C:13]([CH2:12][OH:11])[N:14]=[CH:15]2)[CH:6]=[CH:7][C:2]=1[I:1]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 2,5-diiodofluorobenzene II-4 (2.50 g, 7.18 mmol), 4-hydroxymethylimidazole hydrochloride (0.967 g, 7.18 mmol), 8-hydroxyquinoline (0.104 g, 0.717 mmol) and K2CO3 (2.00 g, 14.5 mmol) in DMSO (12 mL) was degassed with Ar before being charged with CuI (0.136 g, 0.716 mmol). The mixture in a sealed tube was heated at 130° C. overnight. After being cooled to room temperature, H2O and EtOAc were added. It was filtered through celite. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with MeOH in CH2Cl2 (0-5% MeOH) to give (1-(3-fluoro-4-iodophenyl)-1H-imidazol-4-yl)methanol (0.39 g).

Workup

temperatureAfter being cooled to room temperature
filtrationIt was filtered through celite
customThe organic phase was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column
washeluted with MeOH in CH2Cl2 (0-5% MeOH)

Sources & evidence

ORD record: ord-2fe2ab17bf9e4d5c95ff2a1e5a7cddf7
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349873B2

Reaction notes

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