Potassium Phosphate, Tribasic → Methyl 3-[methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylate

HRID 1403463Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[O:10][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:12][CH:13]=2)O1.Cl[C:22]1[C:31]([N:32]([CH3:36])[CH:33]([CH3:35])[CH3:34])=[N:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:37]([O:39][CH3:40])=[O:38])[CH:28]=2)[N:23]=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>[CH3:36][N:32]([CH:33]([CH3:35])[CH3:34])[C:31]1[C:22]([C:9]2[O:10][C:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:12][CH:13]=2)=[N:23][C:24]2[C:29]([N:30]=1)=[CH:28][C:27]([C:37]([O:39][CH3:40])=[O:38])=[CH:26][CH:25]=2

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 4,4,5,5-tetramethyl-2-(5-phenylfuran-2-yl)-1,3,2-dioxaborolane (553 mg, 2.05 mmol) in dioxane (5.5 mL) and water (3 drops) was methyl 2-chloro-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (200 mg, 0.68 mmol), K3PO4 (430 mg, 2.03 mmol) and Pd(PPh3)4 (39.3 mg, 0.03 mmol) with stirring for 1 h at 95° C. in an oil bath under an inert atmosphere of nitrogen. The reaction mixture was concentrated under reduced pressure to give the residue, which was purified by silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford methyl 3-[methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylate as light yellow solid (150 mg, 55%).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customto give the residue, which
customwas purified by silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-779297a8c15348f69c732ac1fefa8ce8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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