Sodium Carbonate → Methyl 3-(isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylate

HRID 1403471Notes

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.CC1(C)C(C)(C)OB([C:29]2[CH:33]=[C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)OC=2)O1.[C:41]([O-])([O-])=[O:42].[Na+].[Na+]>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:14]([N:12]([CH3:13])[C:11]1[C:2]([C:29]2[O:42][CH:41]=[C:32]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:33]=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 (150 mg, 0.51 mmol) in dioxane (5 mL) was added 4,4,5,5-tetramethyl-2-(5-phenylfuran-3-yl)-1,3,2-dioxaborolane (276 mg, 1.02 mmol), Na2CO3 (54 mg, 0.51 mmol), Pd(PPh3)4 (30 mg, 0.03 mmol). The resulting solution was stirred for 1 h at 90° C. and then concentrated in vacuo to give a residue, which was purified by silica gel column chromatography (3.3% ethyl acetate in petroleum ether) to afford methyl 3-(isopropyl(methyl)amino)-2-(4-phenylfuran-2-yl)quinoxaline-6-carboxylate as a red solid (140 mg, 68%).

Workup

concentrationconcentrated in vacuo
customto give a residue, which
customwas purified by silica gel column chromatography (3.3% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-160af99f166a4103914bdd5e84988ab9
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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