Potassium Phosphate, Tribasic → (S)-methyl 2-(4-fluorophenyl)-7-methoxy-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

HRID 1403623Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[C:8]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])[C:9](OS(C(F)(F)F)(=O)=O)=[N:10]2)=[CH:5][C:4]=1[C:27]([O:29][CH3:30])=[O:28].[F:31][C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=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>[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:9]2[C:8]([N:21]3[CH2:25][CH2:24][CH2:23][C@@H:22]3[CH3:26])=[N:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([C:27]([O:29][CH3:30])=[O:28])[CH:5]=3)[N:10]=2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of (S)-methyl 7-methoxy-3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (300 mg, crude) in dioxane (5 ml) and water (3 drops) was added (4-fluorophenyl)boronic acid (280.6 mg, 2.01 mmol), Pd(PPh3)4 (38.5 mg, 0.03 mmol), and K3PO4 (422 mg, 1.99 mmol), and the reaction was stirred for 40 minutes at 95° C. under an atmosphere of nitrogen. The reaction mixture was concentrated in vacuo to give a residue, which was purified via silica gel column chromatography (1% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(4-fluorophenyl)-7-methoxy-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as a light yellow solid (200 mg).

Workup

concentrationThe reaction mixture was concentrated in vacuo
customto give a residue, which
customwas purified via silica gel column chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-02cc840aaa6e4c368e823e0914ebbd41
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

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