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Dimethylformamide → 5-Fluoro-6-methoxy-8-oxo-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carbonitrile

HRID 627681
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 627681
COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.Cl[C:31]1[CH:32]=[N:33][C:34]2[C:35](=[O:44])[NH:36][CH:37]([O:42][CH3:43])[CH:38]([F:41])[C:39]=2[CH:40]=1.[CH3:45][N:46](C=O)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:41][CH:38]1[CH:37]([O:42][CH3:43])[NH:36][C:35](=[O:44])[C:34]2[N:33]=[CH:32][C:31]([C:45]#[N:46])=[CH:40][C:39]1=2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 867157463-chloro-5-fluoro-6-methoxy-6,7-dihydro-1,7-naphthyridin-8(5H)-one

Produkt 1

HCID 867281405-Fluoro-6-methoxy-8-oxo-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carbonitrileAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
Katalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A pressure bottle was charged with Pd2 dba3 (1.032 g, 1.127 mmol), S-Phos (1.157 g, 2.82 mmol), ZnCN2 (2.482 g, 21.14 mmol), 3-chloro-5-fluoro-6-methoxy-6,7-dihydro-1,7-naphthyridin-8(5H)-one (3.25 g, 14.09 mmol) and DMF (70.5 ml). The bottle was purged with argon and sealed, and the reaction mixture was heated at 110° C. for 1 h. Upon cooling to RT the crude reaction mixture was filtered through Celite and washed with MeOH. The filtrate was concentrated. The crude solids were triturated with DCM, filtered, washed with DCM and air-dried. 5-fluoro-6-methoxy-8-oxo-5,6,7,8-tetrahydro-1,7-naphthyridine-3-carbonitrile (2.27 g, 10.26 mmol, 72.8% yield) was isolated as an off white solid. LC/MS (ESI+) m/z=222.0 (M+H).

Aufarbeitung

  1. customThe bottle was purged with argon
  2. customsealed
  3. temperatureUpon cooling to RT the crude
  4. customreaction mixture
  5. filtrationwas filtered through Celite
  6. washwashed with MeOH
  7. concentrationThe filtrate was concentrated
  8. customThe crude solids were triturated with DCM
  9. filtrationfiltered
  10. washwashed with DCM
  11. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-eef7e583e7484870ad0cad26924b982d
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309263B2

Notizen zur Reaktion

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