Toluene → HCID 91618834, compound

HRID 1526232Notes

Reaction equation

HRID 1526232 reaction equation
[Cl:1][C:2]1[C:3](I)=[N:4][CH:5]=[C:6]([Cl:8])[N:7]=1.[CH:10]1(B(O)O)[CH2:12][CH2:11]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>O>[Cl:1][C:2]1[C:3]([CH:10]2[CH2:12][CH2:11]2)=[N:4][CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 156968443,5-Dichloro-2-iodopyrazine

Product 1

HCID 91618834HCID 91618834, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 3,5-dichloro-2-iodopyrazine (2 g), cyclopropylboronic acid (750 mg), tetrakistriphenylphosphine palladium (0) (1.68 g), potassium phosphate (3.09 g), toluene (40 mL), and water (4 mL) was stirred at 110° C. overnight. After leaving to be cooled, the insoluble matter was removed by decantation, followed liquid separation by the addition of ethyl acetate and water. The organic phase was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=98:2) to obtain 3,5-dichloro-2-cyclopropylpyrazine (784 mg) as a colorless oily material.

Workup

  1. customAfter leaving
  2. temperatureto be cooled
  3. customthe insoluble matter was removed by decantation
  4. customliquid separation
  5. additionby the addition of ethyl acetate and water
  6. washThe organic phase was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=98:2)

Sources & evidence

ORD record
ord-d12106c22bc144f7b499f62c69bc7753
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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