Chloropyrazine → 2-(3-Isopropyl-phenyl)-pyrazine

HRID 1392969

Reaction equation

HRID 1392969 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].Cl[C:14]1[CH:19]=[N:18][CH:17]=[CH:16][N:15]=1>C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].C1(C)C=CC=CC=1>[CH:1]([C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[N:18][CH:17]=[CH:16][N:15]=2)[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 73277ChloropyrazineHCID 27734783-Isopropylbenzeneboronic acid

Product 1

HCID 220371202-(3-Isopropyl-phenyl)-pyrazine

Reagents, catalysts & solvents 2

HCID 2724231Bis(1,2-bis(diphenylphosphino)ethane)palladium(0)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of commercial 3-isopropyl-benzene boronic acid (1.0 g) in a 2:2:1 mixture of toluene/1M Na2CO3/EtOH (122 mL), at r.t., 2-chloropyrazine (599 μL) and the bis[1,2-bis(diphenylphosphino)ethane]-palladium(0) catalyst (110 mg) were added. The reaction mixture was heated at 80° C. for 3 hr. It was then cooled down and partitioned between AcOEt/sat.aq. NaCl. The phases were separated and the organic layer was dried. The solids were filtered and the solvent evaporated. The crude oil was purified by flash chromatography (CH/AcOEt 7:3) obtaining the title compound as a clear oil (468 mg).

Workup

  1. temperatureIt was then cooled down
  2. custompartitioned between AcOEt/
  3. customThe phases were separated
  4. customthe organic layer was dried
  5. filtrationThe solids were filtered
  6. customthe solvent evaporated
  7. customThe crude oil was purified by flash chromatography (CH/AcOEt 7:3)

Sources & evidence

ORD record
ord-e71de0d43e3241149b658bbaf7ee3e12
Source dataset
uspto-grants-2008_03
Patent number
US07345041B2

Linked notes

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