1,4-Dioxane → Methyl 3-[methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylate

HRID 1405292Notes

Reaction equation

HRID 1405292 reaction equation
CC1(C)C(C)(C)OB([C:9]2OC=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:13]=2)O1.Cl[C:22]1[C:31]([N:32]([CH3:36])[CH:33]([CH3:35])[CH3:34])=[N:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:37]([O:39][CH3:40])=[O:38])[CH:28]=2)[N:23]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[O:49]1CCOC[CH2:50]1>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>[CH3:36][N:32]([CH:33]([CH3:35])[CH3:34])[C:31]1[C:22]([C:50]2[O:49][C:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:13][CH:9]=2)=[N:23][C:24]2[C:29]([N:30]=1)=[CH:28][C:27]([C:37]([O:39][CH3:40])=[O:38])=[CH:26][CH:25]=2

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 457863484,4,5,5-Tetramethyl-2-(4-phenyl-2-furanyl)-1,3,2-dioxaborolaneHCID 86667203Methyl 2-chloro-3-(isopropyl(methyl)amino)quinoxaline-6-carboxylate

Product 1

HCID 70654220Methyl 3-[methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 4,4,5,5-tetramethyl-2-(4-phenylfuran-2-yl)-1,3,2-dioxaborolane (200 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 (72 mg, 0.25 mmol), K3PO4 (156 mg, 0.73 mmol) and Pd(PPh3)4 (14 mg, 0.01 mmol) with stifling for 1 h at 95° C. in an oil bath which was maintained under an inert atmosphere of nitrogen. The reaction mixture was concentrated under reduced pressure to give the residue, which was purified by silica gel column chromatography eluting with 2% ethyl acetate in petroleum ether to afford methyl 3-[methyl(propan-2-yl)amino]-2-(5-phenylfuran-2-yl)quinoxaline-6-carboxylate as a light yellow solid (50 mg).

Workup

  1. temperaturewhich was maintained under an inert atmosphere of nitrogen
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto give the residue, which
  4. customwas purified by silica gel column chromatography
  5. washeluting with 2% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0291e18a0aa84067869e25ecda50d5df
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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