Ethanol → HCID 90310609, Verbindung

HRID 1524162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524162
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[C:4]([F:11])[C:3]=1[O:12][CH3:13].Br[C:15]1[N:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]2[N:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=2)=[C:4]([F:11])[C:3]=1[O:12][CH3:13]

Komponenten

7

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 68810164HCID 68810164, Verbindung

Produkt 1

HCID 90310609HCID 90310609, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (4-bromo-2-fluoro-3-methoxyphenyl)boronic acid (940 mg, 1.69 mmol) and 5-bromopyrazin-2-amine (1.31 g, 7.56 mmol) was treated with EtOH (12.4 ml), toluene (12.8 ml), and aqueous Na2CO3 (2.0 N, 9.44 ml, 18.9 mmol), and the resulting mixture deoxygenated by sparging with for 10 minutes. Pd(PPh3)4 (218 mg, 0.189 mmol) was then added, and the mixture heated at 80° Celsius for 17 h. The reaction was cooled to rt and then partitioned between saturated aqueous NH4Cl and EtOAc. The organic layer was isolated, dried over MgSO4, and concentrated to dryness. The resultant residue was suspended in DCM and the title compound isolated by filtration (300 mg, 27%), which was used without further purification. Additional product was obtained by concentrating the filtrate to dryness and subjecting the residue to FCC (560 mg, 50%). MS (ESI): mass calcd. for C11HgBrFN3O, 296.99; m/z found, 298.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.34 (dd, J=2.6, 1.5, 1H), 8.00 (d, J=1.5, 1H), 7.54-7.49 (m, 2H), 6.78 (s, 2H), 3.90 (d, J=0.6, 3H).

Aufarbeitung

  1. customthe resulting mixture deoxygenated
  2. customby sparging with for 10 minutes
  3. temperatureThe reaction was cooled to rt
  4. custompartitioned between saturated aqueous NH4Cl and EtOAc
  5. customThe organic layer was isolated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a9a156795661481cb1f56a7884d86e66
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079866B2

Notizen zur Reaktion

Wird geladen…