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 132843Notes

Reaction equation

HRID 132843 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-36e61e2790404ec3a4c37fa866683c5e
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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