(E)-2-styrylbenzo[f][1,7]naphthyridin-5-amine → 2-Phenethylbenzo[f][1,7]naphthyridin-5-amine

HRID 340231Notes

Reaction equation

HRID 340231 reaction equation
[CH:1](/[C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]1=[N:14][C:13]=2[NH2:23])=[CH:2]\[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH2:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([CH:18]=1)=[C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]1=[N:14][C:13]=2[NH2:23])[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 58213554(E)-2-styrylbenzo[f][1,7]naphthyridin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 442306272-Phenethylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of (E)-2-styrylbenzo[f][1,7]naphthyridin-5-amine (Example 32) 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 the crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-80% ethyl acetate in hexane to give 2-phenethylbenzo[f][1,7]naphthyridin-5-amine as a yellow solid. 1H NMR (CDCl3): δ 8.54 (d, 1H), 8.32 (d, 1H), 8.10 (dd, 1H), 7.63 (dd, 1H), 7.51 (m, 1H), 7.03-7.32 (m, 6H), 6.16 (bs, 2H), 3.11 (t, 2H), 2.97 (t, 2H). LRMS [M+H]=300.1.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated en vacuo
  4. customthe crude product was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-9600f4361150424885d39a13bcee9238
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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