Water → Methyl 2-(4-amino-3-nitrophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

HRID 1403518Notes

Reaction equation

[CH:1]([N:4]([CH3:27])[C:5]1[C:6](OS(C(F)(F)F)(=O)=O)=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=2)([CH3:3])[CH3:2].[N+:28]([C:31]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[CH:34][C:32]=1[NH2:33])([O-:30])=[O:29].C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:33][C:32]1[CH:34]=[CH:35][C:36]([C:6]2[C:5]([N:4]([CH:1]([CH3:3])[CH3:2])[CH3:27])=[N:14][C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=3)[N:7]=2)=[CH:37][C:31]=1[N+:28]([O-:30])=[O:29]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-(isopropyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (1.0 g, 2.46 mmol) in DME (10 mL) was added 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.97 g, 3.69 mmol), Pd(PPh3)4 (90 mg, 0.12 mmol), Na2CO3 (781 mg, 7.38 mmol) and water (2 mL) with stirring for 40 minutes at 90° C. under an inert atmosphere of nitrogen in an oil bath. The reaction mixture was concentrated under vacuum to give the residue, which was purified via silica gel chromatography (1% to 5% ethyl acetate in petroleum ether) to afford methyl 2-(4-amino-3-nitrophenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a yellow solid (900 mg, 93%).

Workup

concentrationThe reaction mixture was concentrated under vacuum
customto give the residue, which
customwas purified via silica gel chromatography (1% to 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-42f9a08c47564773b848d8537cdfb469
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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