Iodoethane → (3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one

HRID 898247Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[NH:10][C:9](=[O:18])[C@H:8]1[CH2:19][CH3:20])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:34][CH3:35]>C(#N)C>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[C:5]([N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([F:17])[CH:15]=2)[N:10]([CH2:34][CH3:35])[C:9](=[O:18])[C@H:8]1[CH2:19][CH3:20])=[O:6]

Participants

Conditions

Temperature: 89 °C

Procedure

To a stirred solution of (3R)-4-(2,4-dimethoxybenzoyl)-3-ethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one (0.25 g, 0.73 mmol) in acetonitrile (6 mL) under nitrogen was added cesium carbonate (0.24 g, 0.74 mmol) and iodoethane (0.19 mL, 0.37 g, 2.4 mmol). The mixture was stirred at 89° C. in a sealed tube for 12 h. The solvent was evaporated, and the residue was partitioned between water and methylene chloride. The layers were separated, and the organic layer was washed twice with water, dried over magnesium sulfate, concentrated in vacuo, and purified via Biotage Horizon® (SiO2, gradient from 7% EtOAc/hexane to 51% EtOAc/hexane) to yield 0.20 g (71%) of (3R)-4-(2,4-dimethoxybenzoyl)-1,3-diethyl-6-fluoro-3,4-dihydroquinoxalin-2(1H)-one.

Workup

customThe solvent was evaporated
customthe residue was partitioned between water and methylene chloride
customThe layers were separated
washthe organic layer was washed twice with water
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
custompurified via Biotage Horizon® (SiO2, gradient from 7% EtOAc/hexane to 51% EtOAc/hexane)

Sources & evidence

ORD record: ord-25493bf928c44efcaf7312b16f6447e8
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07351709B2

Reaction notes

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