8-Vinylbenzo[f][1,7]naphthyridin-5-amine → 8-Ethylbenzo[f][1,7]naphthyridin-5-amine

HRID 1479593Notes

Reaction equation

HRID 1479593 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]2=[C:7]3[C:12](=[C:13]([NH2:15])[N:14]=[C:5]2[CH:4]=1)[N:11]=[CH:10][CH:9]=[CH:8]3)=[CH2:2]>CCO.C(Cl)Cl.[Pd]>[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]2=[C:7]3[C:12](=[C:13]([NH2:15])[N:14]=[C:5]2[CH:4]=1)[N:11]=[CH:10][CH:9]=[CH:8]3)[CH3:2]

Participants

5

Reactant 1

HCID 582136728-Vinylbenzo[f][1,7]naphthyridin-5-amine

Product 1

HCID 582135268-Ethylbenzo[f][1,7]naphthyridin-5-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-vinylbenzo[f][1,7]naphthyridin-5-amine (1.0 eq) (from Example 91) and Pd/C (wet, 10% wt) in EtOH was stirred under H2 balloon overnight. The reaction mixture was diluted with DCM. The Pd/C was filtered off through celite, and the filtrate was concentrated en vaccuo to obtain a crude residue. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-60% EtOAc/Hexanes to give 8-ethylbenzo[f][1,7]naphthyridin-5-amine as a white foam: 1H NMR (acetone-d6): δ 8.98 (dd, 1H), 8.88 (dd, 1H), 8.35 (d, 1H), 7.82 (dd, 1H), 7.46 (d, 1H), 7.22 (dd, 1H), 6.63 (br s, 2H), 2.78 (q, 2H), 1.30 (t, 3H). LRMS [M+H]=224.1.

Workup

  1. filtrationThe Pd/C was filtered off through celite
  2. concentrationthe filtrate was concentrated en vaccuo
  3. customto obtain a crude residue
  4. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-5c06a838624d4273a5bc09deb2a4f208
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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