3-Vinylbenzo[f][1,7]naphthyridin-5-amine → 3-Ethylbenzo[f][1,7]naphthyridin-5-amine

HRID 340213Notes

Reaction equation

HRID 340213 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([NH2:17])[N:7]=[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]3=2)[N:4]=1)=[CH2:2].[H][H]>C(OCC)(=O)C.C(O)C.[Pd]>[CH2:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([NH2:17])[N:7]=[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]3=2)[N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 582134833-Vinylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 582137643-Ethylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 3-vinylbenzo[f][1,7]naphthyridin-5-amine (Example 23) in ethyl acetate/ethanol (1:1, 0.07 M) was added 10% wt palladium on carbon (0.2 eq.). Hydrogen gas was introduced via a balloon, and the reaction was stirred overnight. The mixture was filtered through a pad of celite, washing with dichloromethane. The filtrate was concentrated en vacuo giving 3-ethylbenzo[f][1,7]naphthyridin-5-amine as a white solid. 1H NMR (acetone d-6): δ 8.93 (d, 1H), 8.41 (d, 1H), 7.76 (d, 1H), 7.61 (d, 1H), 7.51-7.55 (dd, 1H), 7.30-7.34 (dd, 1H), 6.55 (br, 2H), 6.03 (q, 2H), 1.41 (t, 3H). 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

Sources & evidence

ORD record
ord-fb58d6e197304b38beed8d8cb1662486
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

Loading…