Potassium Phosphate, Tribasic → (S)-methyl 2-(4-fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

HRID 1403576Notes

Reaction equation

[CH3:1][C@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[C:8](OS(C(F)(F)F)(=O)=O)=[N:9][C:10]2[C:15]([N:16]=1)=[CH:14][C:13]([C:17]([O:19][CH3:20])=[O:18])=[CH:12][CH:11]=2.[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[C:32]([CH3:39])[CH:31]=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:29][C:30]1[CH:35]=[CH:34][C:33]([C:8]2[C:7]([N:3]3[CH2:4][CH2:5][CH2:6][C@@H:2]3[CH3:1])=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=3)[N:9]=2)=[C:32]([CH3:39])[CH:31]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (150 mg, 0.41 mmol) in dioxane (5.0 mL) and water (3 drops) was added (4-fluoro-2-methylphenyl)boronic acid (101 mg, 0.66 mmol), Pd(PPh3)4 (19.0 mg, 0.02 mmol), and K3PO4 (138.3 mg, 0.65 mmol). The reaction was stirred for 1 hour at 90° C. under a nitrogen atmosphere. The resulting solution was concentrated in vacuo, and then purified by silica gel column chromatography (1% ethyl acetate in petroleum ether) to provide (S)-methyl 2-(4-fluoro-2-methylphenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as a yellow solid (120 mg, 78%).

Workup

concentrationThe resulting solution was concentrated in vacuo
custompurified by silica gel column chromatography (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-e83a6206a7e94450adce1ad9ce5ddda9
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912188B2

Reaction notes

Loading…