Potassium Phosphate, Tribasic → HCID 86718133, compound

HRID 2205148Notes

Reaction equation

HRID 2205148 reaction equation
Br[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[C:3]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:4][C:5]3[C:10]([N:11]=2)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=3)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 201262(4-Methoxyphenyl)boronic acidHCID 86667202Methyl 3-bromo-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718133HCID 86718133, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Into a 10-mL sealed tube purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (200 mg, 0.58 mmol, 1.00 equiv) in 1,4-dioxane (3 mL). To this was added 4-methoxyphenylboronic acid (133 mg, 0.88 mmol, 1.50 equiv). Addition of Pd2(dba)3 (32 mg, 0.03 mmol, 0.06 equiv) was next. This was followed by the addition of PCy3 (22 mg, 0.08 mmol, 0.14 equiv). To the mixture was added K3PO4 (330 mg, 1.56 mmol, 3.00 equiv). The resulting solution was allowed to react, with stifling, overnight while the temperature was maintained at 110° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:50). This resulted in 160 mg (74%) of methyl 3-(4-methoxyphenyl)-2-phenylquinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customInto a 10-mL sealed tube
  2. custompurged
  3. temperaturemaintained with an inert atmosphere of nitrogen
  4. customto react
  5. concentrationThe resulting mixture was concentrated under vacuum
  6. customThis resulted in 160 mg (74%) of methyl 3-(4-methoxyphenyl)-2-phenylquinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-8cce260cb03b439bac093d47f56b99aa
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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