Potassium Phosphate, Tribasic → HCID 70664633, compound

HRID 1403578Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[C:4]([CH3:11])[CH:3]=1.Cl[C:13]1[C:22]([N:23]([CH3:27])[CH:24]([CH3:26])[CH3:25])=[N:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:28]([O:30][CH3:31])=[O:29])[CH:19]=2)[N:14]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]2[C:22]([N:23]([CH:24]([CH3:26])[CH3:25])[CH3:27])=[N:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:28]([O:30][CH3:31])=[O:29])[CH:19]=3)[N:14]=2)=[C:4]([CH3:11])[CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of (4-fluoro-2-methylphenyl)boronic acid (158 mg, 1.03 mmol) in dioxane (5.0 mL) and water (3 drops) was added methyl 2-chloro-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (100 mg, 0.34 mmol), K3PO4 (215 mg, 1.01 mmol) and Pd(PPh3)4 (20 mg, 0.02 mmol), and the reaction was stirred for 1 hour at 95° C. under an inert atmosphere of nitrogen. The reaction mixture was concentrated in vacuo to provide a residue, which was purified via silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford methyl 2-(4-fluoro-2-methylphenyl)-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate as a light yellow solid (53.0 mg, 42%).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customto provide a residue, which
customwas purified via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-13f08d17fced4ffbbc26208182cd00ee
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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