Sodium Carbonate → (S)-methyl 2-(4-amino-3-nitrophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

HRID 1403526Notes

Reaction equation

[N+:1]([C:4]1[CH:10]=[C:9](B2OC(C)(C)C(C)(C)O2)[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].Cl[C:21]1[C:30]([N:31]2[CH2:35][CH2:34][CH2:33][C@@H:32]2[CH3:36])=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([C:37]([O:39][CH3:40])=[O:38])[CH:27]=2)[N:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:6][C:5]1[CH:7]=[CH:8][C:9]([C:21]2[C:30]([N:31]3[CH2:35][CH2:34][CH2:33][C@@H:32]3[CH3:36])=[N:29][C:28]3[C:23](=[CH:24][CH:25]=[C:26]([C:37]([O:39][CH3:40])=[O:38])[CH:27]=3)[N:22]=2)=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.30 g, 4.92 mmol) in ethylene glycol dimethyl ether (100 mL) was added (S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (1.0 g, 3.27 mmol), sodium carbonate (1.05 g, 9.91 mmol), and Pd(dppf)2Cl2 (0.12 g, 0.17 mmol). The resulting solution was stirred for 40 min at 90° C. under an N2 atmosphere, and then concentrated under vacuum to give a residue, which was purified via silica gel chromatography (2% to 10% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(4-amino-3-nitrophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as an orange solid (1.0 g, 57%).

Workup

concentrationconcentrated under vacuum
customto give a residue, which
customwas purified via silica gel chromatography (2% to 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-37000feff99b40debfb440c3dd841473
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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