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

HRID 559573Notes

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-644ea834527f40268b6482fe0ee57ea7
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063077B2

Reaction notes

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