(4-Methoxyphenyl)boronic acid → 5-Bromo-N-(4-methoxyphenyl)pyrazin-2-amine

HRID 1642272

Reaktionsgleichung

Reaktionsgleichung von HRID 1642272
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Br:12][C:13]1[N:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:12][C:13]1[N:14]=[CH:15][C:16]([NH:19][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:17][CH:18]=1

Komponenten

6

Edukt 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 5995392-Amino-5-bromopyrazine

Produkt 1

HCID 534150715-Bromo-N-(4-methoxyphenyl)pyrazin-2-amineAusbeute 10,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8895Cupric acetateKatalysatorHCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Into a 50 mL roundbottom flask, was placed 4-methoxyphenylboronic acid (5.4 g, 35.54 mmol). To this was added 5-bromo-pyrazin-2-ylamine (3 g, 17.24 mmol). Cu(OAc)2 (3.45 g, 19.06 mmol) was added, followed by addition of a solution of DMAP (4.2 g, 34.43 mmol) in CH2Cl2 (20 mL). The resulting solution was stirred at room temperature for 12 hours. The reaction progress was monitored by thin layer chromatography (TLC) (ethyl acetate/petroleum ether=1:2). When the reaction was complete, the mixture was filtered, then concentrated under vacuum. The residue was dissolved in ethyl acetate (EtOAc), then washed with water. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by silica gel chromatography (SGC) eluting with ethyl acetate/petroleum ether (1:5, v/v) to provide (5-bromo-pyrazin-2-yl)-(4-methoxy-phenyl)-amine (i) (500 mg, yield 10%) as a yellow solid.

Aufarbeitung

  1. customInto a 50 mL roundbottom flask, was placed
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate (EtOAc)
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel chromatography (SGC)
  10. washeluting with ethyl acetate/petroleum ether (1:5

Quellen und Nachweise

ORD-Eintrag
ord-425ee4b87c6f4d188a081842f9a4f50e
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08119643B2

Verknüpfte Notizen

Wird geladen…