(E)-8-methyl-2-(prop-1-enyl)benzo[f][1,7]naphthyridin-5-amine → 8-Methyl-2-propylbenzo[f][1,7]naphthyridin-5-amine

HRID 340251Notes

Reaction equation

HRID 340251 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][C:5]2=[C:6]3[C:11](=[C:12]([NH2:14])[N:13]=[C:4]2[CH:3]=1)[N:10]=[CH:9][C:8](/[CH:15]=[CH:16]/[CH3:17])=[CH:7]3.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][C:2]1[CH:19]=[CH:18][C:5]2=[C:6]3[C:11](=[C:12]([NH2:14])[N:13]=[C:4]2[CH:3]=1)[N:10]=[CH:9][C:8]([CH2:15][CH2:16][CH3:17])=[CH:7]3

Participants

5

Reactant 2

HCID 66890437(E)-8-methyl-2-(prop-1-enyl)benzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 582135528-Methyl-2-propylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of (E)-8-methyl-2-(prop-1-enyl)benzo[f][1,7]naphthyridin-5-amine (from the previous step) 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 stirred 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 8-methyl-2-propylbenzo[f][1,7]naphthyridin-5-amine as offwhite solid. 1H NMR (CDCl3): δ 8.59 (d, 1H), 8.41 (d, 1H), 8.10 (d, 1H), 7.43 (s, 1H), 7.13 (dd, 1H), 5.94 (bs, 2H), 2.78 (t, 2H), 2.44 (s, 3H), 1.75 (m, 2H), 0.95 (t, 3H). LRMS [M+H]=252.1

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-75f79e9bece541cea3102b74b4b467fa
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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