Potassium Phosphate, Tribasic → Methyl 2-[5-(4-fluorophenyl)furan-2-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate

HRID 1403484Notes

Reaction equation

HRID 1403484 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11](B3OC(C)(C)C(C)(C)O3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[C:23]1[C:32]([N:33]([CH3:37])[CH:34]([CH3:36])[CH3:35])=[N:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:38]([O:40][CH3:41])=[O:39])[CH:29]=2)[N:24]=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:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([C:23]3[C:32]([N:33]([CH3:37])[CH:34]([CH3:35])[CH3:36])=[N:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:38]([O:40][CH3:41])=[O:39])[CH:29]=4)[N:24]=3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 70665171HCID 70665171, compoundHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 70665195Methyl 2-[5-(4-fluorophenyl)furan-2-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylateYield 70.1%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
90 °C

Procedure

To a solution of 2-[5-(4-fluorophenyl)furan-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (442 mg, crude) in dioxane (5.5 mL) and water (3 drops) was added methyl 2-chloro-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate (150 mg, 0.51 mmol), K3PO4 (324.9 mg, 1.53 mmol) and Pd(PPh3)4 (29.5 mg, 0.03 mmol) with stirring for 40 min at 90° C. in an oil bath maintained under an inert atmosphere of nitrogen. The reaction mixture was concentrated under reduced pressure to give the residue, which was purified via silica gel chromatography (2% ethyl acetate in petroleum ether) to afford methyl 2-[5-(4-fluorophenyl)furan-2-yl]-3-[methyl(propan-2-yl)amino]quinoxaline-6-carboxylate as light yellow solid (150 mg, 55%).

Workup

  1. temperaturemaintained under an inert atmosphere of nitrogen
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give the residue, which
  4. customwas purified via silica gel chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-af9660a8286e438a987976d417a9906a
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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