Potassium Carbonate → 1-(4,5-Dichloro-1-imidazolyl)methyl-2-ethoxycarbonyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one

HRID 1599418Notes

Reaction equation

Br[CH2:2][C:3]1[N:7]2[C:8]3[C:13]([NH:14][C:15](=[O:16])[C:6]2=[N:5][C:4]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][CH:9]=3.[Cl:26][C:27]1[N:28]=[CH:29][NH:30][C:31]=1[Cl:32].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:26][C:27]1[N:28]=[CH:29][N:30]([CH2:2][C:3]2[N:7]3[C:8]4[C:13]([NH:14][C:15](=[O:16])[C:6]3=[N:5][C:4]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:12][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:10][CH:9]=4)[C:31]=1[Cl:32]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 1-bromomethyl-2-ethoxycarbonyl-7-trifluoromethylimidazo[1,2-a]quinoxalin-4(5H)-one (Example 3) (2.1 g, 5.0 mmol), 4,5-dichloroimidazole (1.5 g, 11.0 mmol) and potassium carbonate (1.5 g, 11 mmol) in acetonitril (100 ml) was stirred at 80° C. for 5 h and overnight at room temperature. The solvent was evaporated in vacuo and the residue submitted to flash chromatography on silica gel 60 eluting with dichloromethane/methanole (19:1) to give 540 mg (23%) of the title compound. M.p. 240° C.

Workup

customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-ec8175a115464abb9f2aea9961443984
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741785

Reaction notes

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