Potassium Phosphate, Tribasic → HCID 70664711, compound

HRID 1403489Notes

Reaction equation

Cl[C:2]1[C:11]([N:12]([CH3:16])[CH:13]([CH3:15])[CH3:14])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:17]([O:19][CH3:20])=[O:18])[CH:8]=2)[N:3]=1.CC1(C)C(C)(C)OB([C:29]2[CH:30]=[CH:31][C:32]3[O:36][CH:35]=[C:34]([CH3:37])[C:33]=3[CH:38]=2)O1.[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>[CH3:16][N:12]([CH:13]([CH3:15])[CH3:14])[C:11]1[C:2]([C:29]2[CH:30]=[CH:31][C:32]3[O:36][CH:35]=[C:34]([CH3:37])[C:33]=3[CH:38]=2)=[N:3][C:4]2[C:9]([N:10]=1)=[CH:8][C:7]([C:17]([O:19][CH3:20])=[O:18])=[CH:6][CH:5]=2

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 2-chloro-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (150 mg, 0.36 mmol) in 1,4-dioxane (6 mL) was added 4,4,5,5-tetramethyl-2-(3-methyl-1-benzofuran-5-yl)-1,3,2-dioxaborolane (350 mg, 1.36 mmol), Pd(PPh3)4 (40 mg, 0.034 mmol), K3PO4 (430 mg, 2.04 mmol) and water (5 drops) with stirring for 5 h 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 3-[methyl(propan-2-yl)amino]-2-(3-methyl-1-benzofuran-5-yl)quinoxaline-6-carboxylate as a yellow solid (110 mg, 63%).

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-0ca2ad120c844413b1dc3ed9c16db491
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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