tert-Butyl Methyl [3-Cyano-5-(trifluoromethyl)pyridin-2-yl]malonate → Tert-butyl 7-oxo-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-8-carboxylate

HRID 132843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 132843
[C:1]([C:3]1[C:4]([CH:13]([C:21](OC)=[O:22])[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N:5][CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)#[N:2].[H][H]>[Ni].C(O)C>[O:22]=[C:21]1[CH:13]([C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[C:4]2[N:5]=[CH:6][C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:3]=2[CH2:1][NH:2]1

Komponenten

5

Edukt 2

HCID 59017435tert-Butyl Methyl [3-Cyano-5-(trifluoromethyl)pyridin-2-yl]malonateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 59017436Tert-butyl 7-oxo-3-(trifluoromethyl)-5,6,7,8-tetrahydro-1,6-naphthyridine-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of Raney nickel (1 g) and the product from Step E above (18.2 g, 52.9 mmol) in ethanol (130 mL) was placed on a Parr shaker apparatus and hydrogenated at 40 psi hydrogen overnight. The suspension was filtered through Celite and the filtrate was evaporated in vacuo to afford the title compound. 1H NMR (500 MHz, CDCl3) δ 8.83 (s, 1H), 7.89 (s, 1H), 7.82 (s, 1H), 4.83 (d, J=16 Hz, 1H), 4.72 (s, 1H), 4.49 (d, J=16 Hz, 1H), 1.45 (s, 9H).

Aufarbeitung

  1. filtrationThe suspension was filtered through Celite
  2. customthe filtrate was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-36e61e2790404ec3a4c37fa866683c5e
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07388019B2

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