8-Hydroxyquinoline → 1-(4-(4-(hydroxymethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one

HRID 1802609Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])=[CH:4][CH:3]=1.[OH:15][CH2:16][C:17]1[N:18]=[CH:19][NH:20][CH:21]=1.OC1C=CC=C2C=1N=CC=C2.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.[Cu]I.CCOC(C)=O.O>[OH:15][CH2:16][C:17]1[N:18]=[CH:19][N:20]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]3=[O:14])=[CH:4][CH:3]=2)[CH:21]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 1-(4-iodophenyl)pyridin-2(1H)-one prepared in Example 19 (1.00 g, 3.37 mmol), 4-hydroxymethylimidazole II-1 (0.330 g, 3.37 mmol), 8-hydroxyquinoline (0.073 g, 0.50 mmol) and K2CO3 (1.00 g, 7.25 mmol) in DMSO (7 mL) was degassed with Ar before being charged with CuI (0.100 g, 0.52 mmol). The mixture in a sealed tube was heated at 130° C. overnight. Water and EtOAc were added. The mixture was filtered through CELITE. The organic layer was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by HPLC to give 1-(4-(4-(hydroxymethyl)-1H-imidazol-1-yl)phenyl)pyridin-2(1H)-one (335 mg). MS 268 (M+H).

Workup

customwas degassed with Ar
filtrationThe mixture was filtered through CELITE
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-ee765bb166014eff9b13612cb0527d57
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349873B2

Reaction notes

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