Potassium Phosphate, Tribasic → HCID 70665301, compound

HRID 1403658Notes

Reaction equation

HRID 1403658 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:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[F:36].[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:31]=[C:32]([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)[CH:33]=[CH:34][C:35]=1[F:36]

Participants

8

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343373,4-Difluorobenzeneboronic acidHCID 86670557(S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate

Product 1

HCID 70665301HCID 70665301, compoundYield 48.2%

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (S)-methyl 3-(2-methylpyrrolidin-1-yl)-2-(trifluoromethylsulfonyloxy)quinoxaline-6-carboxylate (195 mg, crude) in dioxane (3 mL) was added 3,4-difluorophenylboronic acid (130 mg, 0.80 mmol), K3PO4 (180 mg, 0.8 mmol), Pd(PPh3)4 (28 mg, 0.024 mmol) and water (5 drops) under a nitrogen atmosphere. After stirring 1 h at 90° C., the reaction mixture was dissolved in water (100 mL), extracted with dichloromethane (3×30 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford a residue, which was purified via silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(3,4-difluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as a light yellow solid (86.0 mg).

Workup

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford a residue, which
  5. customwas purified via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-f6888df379d74b9ea7be259bf6108710
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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