Potassium Carbonate → HCID 68630938, compound

HRID 1801476Notes

Reaction equation

HRID 1801476 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[N:8]2.C([O-])([O-])=O.[K+].[K+].O1CCO[CH2:23][CH2:22]1>O>[CH2:2]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[N:8]2)[CH:22]=[CH2:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 66737742HCID 66737742, compound

Product 1

HCID 68630938HCID 68630938, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 8-(bromomethyl)-2-methoxy-quinoxaline (8.0 g; prepared according to WO 2008/078305) and K2CO3 (8.74 g) in dioxane (154 mL) and water (20 mL) was degassed by bubbling N2 through for 20 min and treated with Pd(dppf)Cl2.DCM complex (1:1) (521 mg) and vinylboronic anhydride pyridine complex (5.12 g). The reaction was further stirred at 110° C. for 2 days and partitioned between water and ether. The org. phase was washed with water and brine, dried over MgSO4, concentrated under reduced pressure and purified by CC (Hex/EA 9:1 to 4:1), affording a yellow liquid (4.70 g, 74% yield).

Workup

  1. customwas degassed
  2. customby bubbling N2 through for 20 min
  3. additiontreated with Pd(dppf)Cl2
  4. custompartitioned between water and ether
  5. washphase was washed with water and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. custompurified by CC (Hex/EA 9:1 to 4:1)

Sources & evidence

ORD record
ord-880b144f84d441c1aedd94a104f74717
Source dataset
uspto-grants-2013_01
Patent number
US08349828B2

Reaction notes

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