Water → 3-(4-chlorophenyl)-1-ethyl-quinoxalin-2(1H)-one

HRID 76364Notes

Reaction equation

Br[C:2]1[C:3](=[O:14])[N:4]([CH2:12][CH3:13])[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:3](=[O:14])[N:4]([CH2:12][CH3:13])[C:5]3[C:10]([N:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To 200 mg (0.79 mM) of 3-bromo-1-ethyl-quinoxalin-2(1H)-one and 27.7 mg (0.04 mM) of bis(triphenylphosphine)palladium (II) chloride in 1 ml of dimethylformamide were added under nitrogen 185.3 mg (1,185 mM) of 4-chlorophenylboronic acid and 0.8 ml (1.6 mM) of a 2M sodium carbonate aqueous solution. The reaction mixture was heated to 90° C. and stirred for 30 min under nitrogen atmosphere. Water was added and the mixture was extracted with ethyl acetate. The organic phase was separated, dried over anhydrous sodium sulfate, and concentrated. The compound was purified through a silica plug eluting with dichloromethane, which afforded after evaporation 132 mg of 3-(4-chlorophenyl)-1-ethyl-quinoxaline-2(1H)-one as a solid. Yield: 59%.

Workup

extractionthe mixture was extracted with ethyl acetate
customThe organic phase was separated
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe compound was purified through a silica plug
washeluting with dichloromethane, which
customafforded
customafter evaporation 132 mg of 3-(4-chlorophenyl)-1-ethyl-quinoxaline-2(1H)-one as a solid

Sources & evidence

ORD record: ord-c7c43956094d420597a800ddcb74d979
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835634B2

Reaction notes

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