2-Vinylbenzo[f][1,7]naphthyridin-5-amine → 2-Ethylbenzo[f][1,7]naphthyridin-5-amine

HRID 340226Notes

Reaction equation

HRID 340226 reaction equation
[CH:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]1=[N:8][C:7]=2[NH2:17])=[CH2:2].[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]1=[N:8][C:7]=2[NH2:17])[CH3:2]

Participants

5

Reactant 2

HCID 582136672-Vinylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 442322642-Ethylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 2-vinylbenzo[f][1,7]naphthyridin-5-amine (Example 29) in ethyl acetate/methanol (1:4, 0.05 M) was added 10% wt palladium on carbon (0.2 eq.). Hydrogen gas was introduced via a balloon, and the reaction was stiffed for 3 hours. The mixture was filtered through a pad of celite, washing with dichloromethane. The filtrate was concentrated en vacuo and purified by a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 2-ethylbenzo[f][1,7]naphthyridin-5-amine as a solid. 1H NMR (methanol-d4): δ 8.78-8.81 (m, 2H), 8.45 (d, 1H), 7.55-7.63 (m, 2H), 7.35-7.40 (m, 1H), 2.97 (q, 2H), 1.43 (t, 2H). LRMS [M+H]=224.1.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated en vacuo
  4. custompurified by a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-6b85b38c8e424ca3a6912745702a8df6
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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