Potassium Phosphate, Tribasic → HCID 70664687, compound

HRID 1403298Notes

Reaction equation

Cl[C:2]1[C:11]([N:12]([CH:14]([CH3:16])[CH3:15])[CH3:13])=[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.[NH:21]1[CH:25]=[C:24](B(O)O)[CH:23]=[N:22]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>[CH:14]([N:12]([CH3:13])[C:11]1[C:2]([C:24]2[CH:25]=[N:21][NH:22][CH:23]=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)([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate (Scheme I, 200.0 mg, 0.68 mmol) in dioxane (3 mL) was added 1H-pyrazol-4-ylboronic acid (172.0 mg, 1.54 mmol), K3PO4 (326.0 mg, 1.54 mmol), Pd(PPh3)4 (29.6 mg, 0.03 mmol) and 3 drops water. The resulting solution was stirred for 20 min at 90° C. with an inert atmosphere of nitrogen and then diluted with water (20 mL), extracted with dichloromethane (4×20 mL), dried over anhydrous magnesium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 2%-10% ethyl acetate in petroleum ether to afford methyl 3-(isopropyl(methyl)amino)-2-(1H-pyrazol-4-yl)quinoxaline-6-carboxylate as a yellow solid (130 mg, 58.6%).

Workup

extractionextracted with dichloromethane (4×20 mL)
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by a silica gel column with 2%-10% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-674b920558eb4525a68d8b52bcb6e58e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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