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

HRID 1403401Notes

Reaction equation

HRID 1403401 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

Conditions

Temperature
95 °C

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 stirring 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. temperaturewas 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-34cebae32ac64ca99dfacd89e5c1502a
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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