Sodium Carbonate → HCID 59472154, Verbindung

HRID 78564

Reaktionsgleichung

Reaktionsgleichung von HRID 78564
[NH2:1][C:2]1[C:3]([C:9]([O:11]C)=[O:10])=[N:4][C:5](Br)=[CH:6][N:7]=1.C(B(CC)[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.Cl[Pd]Cl.CCOC(C)=O>[NH2:1][C:2]1[C:3]([C:9]([OH:11])=[O:10])=[N:4][C:5]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)=[CH:6][N:7]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 227251Methyl 3-Amino-6-bromopyrazine-2-carboxylateHCID 6428513-(Diethylboryl)pyridine

Produkt 1

HCID 59472154HCID 59472154, VerbindungAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24290Palladium ChlorideKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (8 g, 34.48 mmol), diethyl-(3-pyridyl)borane (6.084 g, 41.38 mmol), dichloropalladium; triphenylphosphane (1.210 g, 1.724 mmol) and disodium carbonate (51.70 mL of 2 M, 103.4 mmol) in DME (100 mL) were heated overnight at 80° C. The reaction mixture was cooled and EtOAc was added. The resultant precipitate was collected, treated with water and the resultant suspension heated and filtered hot. The solution was then allowed to cool and acidified with AcOH to approx pH 5. The precipitate was collected, washed with MeOH and dried to yield the product as a yellow powder (6.22 g, 83% Yield). 1H NMR (400.0 MHz, DMSO) d 7.49 (dd, J=4.8, 7.4 Hz, 1H), 7.60 (s, 2H), 8.44 (d, J=7.6 Hz, 1H), 8.57 (d, J=3.7 Hz, 1H), 8.97 (s, 1H) and 9.27 (s, 1H) ppm; MS (ES+) 217

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customThe resultant precipitate was collected
  3. additiontreated with water
  4. temperaturethe resultant suspension heated
  5. filtrationfiltered hot
  6. temperatureto cool
  7. customThe precipitate was collected
  8. washwashed with MeOH
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-90c9a609f1164fa2800eafbbc9caf6e9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841308B2

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