4-Chloroaniline → HCID 58026182, compound

HRID 1961697Notes

Reaction equation

HRID 1961697 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1.CC(C)([O-])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:9][C:10]1[CH:16]=[CH:15][C:13]([NH:14][C:2]2[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 785042,6-DichloropyrazineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 58026182HCID 58026182, compoundYield 19.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,6-dichloropyrazine (2.0 g, 13.4 mmol), 4-chloroaniline (1.88 g, 14.8 mmol) and sodium tert-butoxide (1.71 g, 17.6 mmol) in toluene (45 mL) were degassed with argon for 20 minutes. (±)-2,2′-Bis(diphenylphosphino-)1,1′-binaphthalene ((±)-BINAP) (502 mg, 0.81 mmol) and palladium(II)-acetate (90.4 mg, 0.40 mmol) were added followed by degassing for 5 minutes. The reaction mixture was stirred at 100° C. over night. The mixture was filtrated and the filtrate evaporated. Flash chromatography (ethyl acetate/heptane as eluent) gave (4-chloro-phenyl)-(6-chloro-pyrazin-2-yl)-amine (628 mg, 18%) as a brown oil.

Workup

  1. customwere degassed with argon for 20 minutes
  2. customby degassing for 5 minutes
  3. filtrationThe mixture was filtrated
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-55ed7aeafc214821830a1eefe03ba437
Source dataset
uspto-grants-2013_04
Patent number
US08415358B2

Reaction notes

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