Potassium Phosphate, Tribasic → methyl 3-(cyclopropyl(methyl)amino)-2-(1H-indazol-5-yl)quinoxaline-6-carboxylate

HRID 1403365Notes

Reaction equation

[CH:1]1([N:4]([CH3:27])[C:5]2[C:6](OS(C(F)(F)F)(=O)=O)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH2:2]1.[NH:28]1[C:36]2[C:31](=[CH:32][C:33](B(O)O)=[CH:34][CH:35]=2)[CH:30]=[N:29]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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:1]1([N:4]([CH3:27])[C:5]2[C:6]([C:33]3[CH:32]=[C:31]4[C:36](=[CH:35][CH:34]=3)[NH:28][N:29]=[CH:30]4)=[N:7][C:8]3[C:13]([N:14]=2)=[CH:12][C:11]([C:15]([O:17][CH3:18])=[O:16])=[CH:10][CH:9]=3)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of methyl 3-(cyclopropyl(methyl)amino)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (300 mg, crude) in dioxane (10 mL), 1H-indazol-5-ylboronic acid (430 mg, 1.76 mmol), K3PO4 (370 mg, 1.76 mmol), and Pd(PPh3)4 (51 mg, 0.04 mmol). The resulting solution was stirred for 1 h at 90° C. The resulting mixture was concentrated under vacuum to give a residue, which was purified by a silica gel column with 5%-50% ethyl acetate in petroleum ether to afford methyl 3-(cyclopropyl(methyl)amino)-2-(1H-indazol-5-yl)quinoxaline-6-carboxylate as a yellow solid (40 mg).

Workup

concentrationThe resulting mixture was concentrated under vacuum
customto give a residue, which
customwas purified by a silica gel column with 5%-50% ethyl acetate in petroleum ether

Sources & evidence

ORD record: ord-296b58927e90480caedb228c6c7fbb0f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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